Catalysis Research is an international peer-reviewed Open Access journal published quarterly online by LIDSEN Publishing Inc. This periodical is devoted to publishing high-quality papers that describe the most significant and cutting-edge research in all areas of catalysts and catalyzed reactions. Its aim is to provide timely, authoritative introductions to current thinking, developments and research in carefully selected topics.

Topics contain but are not limited to:

  • Photocatalysis
  • Electrocatalysis
  • Environmental catalysis
  • Biocatalysis, enzymes, enzyme catalysis
  • Catalysis for biomass conversion
  • Organocatalysis, catalysis in organic and polymer chemistry
  • Nanostructured Catalysts
  • Catalytic materials
  • Computational catalysis
  • Kinetics of catalytic reactions

It publishes a variety of article types: Original Research, Review, Communication, Opinion, Comment, Conference Report, Technical Note, Book Review, etc.

There is no restriction on paper length, provided that the text is concise and comprehensive. Authors should present their results in as much detail as possible, as reviewers are encouraged to emphasize scientific rigor and reproducibility.

Indexing: 

Publication Speed (median values for papers published in 2023): Submission to First Decision: 4.1 weeks; Submission to Acceptance: 13.0 weeks; Acceptance to Publication: 9 days (1-2 days of FREE language polishing included)

Current Issue: 2024  Archive: 2023 2022 2021
Open Access Original Research

Zn(OCOCH3)2·2H2O Catalysed Efficient Preparation of 2-Phenyl-4-Arylmethylidene-5-Oxazolinones under Ultrasonic Condition

Sadeq Hamood Saleh Azzam 1, Amreen Khanum 2, Mohamed Afzal Pasha 2,*

  1. Department of Chemistry, Faculty of Science, Sana’a University, YEMEN

  2. Department of Studies in Chemistry, Jnanabharathi Campus, Bangalore University, Bengaluru-560 056, INDIA

Correspondence: Mohamed Afzal Pasha

Academic Editor: Antonio Monopoli

Special Issue: Applied Catalysis for a Circular Economy

Received: September 30, 2022 | Accepted: January 30, 2023 | Published: February 15, 2023

Catalysis Research 2023, Volume 3, Issue 1, doi:10.21926/cr.2301007

Recommended citation: Azzam SHS, Khanum A, Pasha MA. Zn(OCOCH3)2·2H2O Catalysed Efficient Preparation of 2-Phenyl-4-Arylmethylidene-5-Oxazolinones under Ultrasonic Condition. Catalysis Research 2023;3(1):12; doi:10.21926/cr.2301007.

© 2023 by the authors. This is an open access article distributed under the conditions of the Creative Commons by Attribution License, which permits unrestricted use, distribution, and reproduction in any medium or format, provided the original work is correctly cited.

Abstract

2-Phenyl-4-arylmethylidene-5-oxazolinones were synthesized in very high yield by subjecting a mixture of an aryl aldehyde/heterocyclic aldehyde/cinnamaldehyde and hippuric acid in anhydrous acetic anhydride and catalytic Zn(OCOCH3)2·2H2O to ultrasonication at 35 KHz for 4 to 8 min. This method has many advantages: use of a green catalyst; yields are high, involves easy workup procedure, is energy efficient and economically feasible.

Graphical abstract

Click to view original image

Keywords

2-phenyl-4-arylmethylidene-5-oxazolinones; Zn(OCOCH3)2•2H2O; hippuric acid; araldehydes; acetic anhydride; ultrasonication

1. Introduction

2-Phenyl-4-aryl methylidene-5-oxazolinones are important in synthesizing fine chemicals and serve as precursors for biologically active molecules such as: unsaturated amino acids, peptides and biosensors [1]. Oxazolin-5-ones are multifunctional due to the presence of C=C, C=N, and C=O bonds. Hence, they are important in the synthesis of natural products and pharmaceutical chemicals [2,3].

Substituted oxazoles are important as they are compatible in the preparation of biologically active molecules such as: anti-bacterial, antifungal, anti-inflammatory [2,3,4], analgesic [5], anticancer [6,7], anti-diabetic [8] and antiobesity [9] agents. Further, 2-phenyl-4-aryl methylidene-5-oxazolinones are useful for the synthesis of thiadiazoles and triazoles [10] which also exhibit antimycobacterial [11,12], antimycotic [13] and antidepressive [14] activities. Oxazoles are further used as fluorescent whitening agents, dyes, pigments and lubricants [15,16,17,18].

The development of methods for azlactones is still an active field of investigation. Erlenmeyer Plöchl's reaction of an aldehyde, hippuric acid in acetic anhydride by using sodium acetate as a catalyst is well known [19]. Erlenmeyer Plöchl reaction has remained unchanged since the last century with some modification of catalysts such as: zwitter ionic imidazolium salt [20], [Yb(OTf)3] [21], [TCT,PPh3] [22], [TsCl/DMF] [23], nano-sphere SiO2–AP [24], AcOK [25], Montmorillonite K-10 [26], MgO/Al2O3 [27], KF-Al2O3 [28], silica–alumina supported heteropolyacids [29], Nano Fe2O3 [30], Ca(OAc)2 [31], Bi(III) Salts [32], [CellFemImi]OH [33], [bmim]3PW12O40 [34], [bmim]PF6 or [bmim]BF4 [35]. However, some of these methods have their excellence, but, suffer from drawbacks such as: high temperature, low yields, generation of toxic substances, and use of stoichiometric catalysts.

Sonochemistry has received attention in the past two decades. The driving force of ultrasonic reactions has many facets: The method is energy efficient, hence, is economical, the reactions can be scaled up using ultrasonic reactors; there is a need for a technology that minimizes the waste [36].

2. Results & Discussion

In continuation of our work on the preparation of oxazolin-5-ones using iodine as a catalyst under microwave irradiation [37], and the use of nano MgO under sonic condition [38], which have got their own advantages; and in continuation of our work on ultrasound-assisted reactions [39,40,41,42,43,44,45,46,47] we, herein, report another energy efficient synthesis of oxazolin-5-ones from hippuric acid, aryl aldehydes/heterocyclic aldehyde (furfural)/cinnamaldehyde and acetic anhydride in the presence of readily available, green and highly economical catalyst Zn(OCOCH3)2·2H2O under the sonic condition as shown in the Scheme1.

Click to view original image

Scheme 1 Preparation of 2-phenyl-4-substitutedmethylidene-5-oxazolinones using catalytic Zn(OCOCH3)2·2H2O under sonic condition.

To evaluate the suitability of Zn(OCOCH3)2·2H2O, and to establish its catalytic role in the synthesis of biologically important oxazoline-5-ones, we initiated the present study at room temperature using hippuric acid, aryl aldehydes/heterocyclic aldehyde/cinnamaldehyde and acetic anhydride in EtOH as a solvent.

Several catalysts were examined for oxazoline-5-ones synthesis; to find the correct condition, a control reaction was carried out without a catalyst to get 5% product as presented in Table 1 (entry 1). Furthermore, to optimize the reaction conditions, we executed the reaction of 4-chlorobenzaldehyde with hippuric acid in acetic anhydride and Zn(OCOCH3)2·2H2O as an activator under diverse reaction environments such as: mechanical stirring, grinding, heating, refluxing in Ethanol, and under sonic condition. Grinding of the reactants with Zn(OCOCH3)2·2H2O gave a low yield (entry 14). On further investigation, we found that, the product yield is low under different conditions. Delightfully, Zn(OCOCH3)2·2H2O efficiently promoted the transformation under ultrasonic condition showing the highest degree of conversion, as it gave a very high yield in a short time (Table 1, entry 16). When the reaction was carried out under ultrasonication, the product was obtained in 95% yield within 8 min. The obtained results have been compared with some of the available methods in the literature for the preparation of 5-oxazolinones and the details are presented in Table 1.

Table 1 Synthesis of 2-Phenyl-4-(4'-chlorophenylmethylidene)-5-oxazolinone under varied conditions.

After examining the various reaction parameters, we examined the substrate scope and efficiency of the reaction with aryl/het(aryl)/cinnamyl aldehydes having electron withdrawing and electron donating groups in their aromatic rings, to get the corresponding products in very good to high yields under optimized reaction conditions as shown in Table 2. The 1HNMR spectra of all the prepared 5-oxazolinones showed characteristic methylidene proton signal between δ 7.22 and 8.37 ppm. The azalactone carbonyl group showed a strong signal in the IR spectra between υ 1797 to 1785 cm-1 of all the prepared products.

Table 2 Conversion of aryl aldehydes/furfural/cinnamaldehyde into the corresponding 2-phenyl-4-substitutedmethylidene-5-oxazolinones using catalytic Zn(OCOCH3)2·2H2O under sonic condition.

3. Methods

3.1 Materials and Instruments

Zn(OCOCH3)2·2H2O, acetic anhydride, aryl aldehydes/furfural/cinnamaldehyde, hippuric acid and other chemicals are commercial. Silica gel G254 TLC regulated the reactions under a UV lamp. The reactions were studied in a sonic bath at 35 kHz at 25°C. The IR spectra were recorded using a SHIMADZU FT-IR-8400S instrument, and 1HNMR spectra on a 400 MHz Bruker spectrophotometer in CDCl3 as a solvent.

3.2 General Procedure

Two mmol each of aryl aldehyde/furfural/ cinnamaldehyde, hippuric acid, 4 mmol of acetic anhydride and 0.5 mmol Zn(OCOCH3)2·2H2O in 3 mL ethanol were integrated well, and shrilled in the sonic bath for 4‒8 min (Table 2). The crude product was filtered, washed with hot water and recrystallized from methanol-water (2:1) to get 90–95% product.

3.3 Spectral Data

3.3.1 2-Phenyl-4-(4'-Methoxyphenylmethylidene)-5-Oxazolinone (3a): [48]

IR (KBr): ν C=O 1787.89 cm-1.

1H NMR (400 MHz, CDCl3): δ 3.87 (s, 3H), 6.95–6.99 (d, 2H, J = 8.8 Hz), 7.26 (s, 1H, =C-H), 7.43–7.57 (m, 3H), 8.18–8.19 (m, 2H), 8.21 (d, 2H, J = 8.8 Hz) ppm.

13C NMR (100 MHz, CDCl3): δ 55.56, 113.74, 114.53, 127.06, 128.1, 128.8, 131.8, 132.31, 134.58, 162.2, 167.9 ppm.

3.3.2 2-Phenyl-4-Benzylidene-5-Oxazolinone (3b): [48]

IR (KBr): ν C=O 1790 cm-1.

1H NMR (400 MHz, CDCl3): δ 7.26 (s, 1H, =C-H), 7.46–7.64 (m, 5H, ArH), 8.18–8.23 (m, 5H, ArH) ppm.

13C NMR (100 MHz, CDCl3): δ125.63, 128.40, 128.91, 131.20, 131.80, 132.47, 133.36, 133.55 ppm.

3.3.3 4-(4'-Nitropheylmethylidene)-5-Oxazolinone (3c): [49]

IR (KBr): ν C=O 1785.53 cm-1.

1H NMR (400 MHz, CDCl3): δ 7.36 (s, 1H, =C-H), 7.62–8.05 (m, 5H, ArH), 7.96 (dd, 2H, H-2′ and H-6′), 8.20 (dd, 2H, H-3′ and H-5′) ppm.

13C NMR (100 MHz, CDCl3): δ 118.5, 126.9, 128.3, 129.2, 131.1, 132.4, 134.8, 138.2, 142.6, 147.5, 161.7, 173.2 ppm

MS (ESI) m/z: 294.06 [M+H]+•.

3.3.4 2-Phenyl-4-(3′,4′-Dimethoxyphenylmethylidene)-5-Oxazolinone (3d):

IR (KBr): ν C=O 1785.96 cm-1.

1HMR (400 MHz, CDCl3): δ 3.98 (s, 3H), 4.04 (s, 3H), 6.95 (d, 1H, J = 9 .2) 7.22 (s, 1H, =C-H), 7.55 (m, 4H, J = 8.4 Hz), 8.15 (s, 1H), 8.19 (d, 2H, J = 9.6 Hz) ppm.

13C NMR (100 MHz, CDCl3): δ 110.91, 113.98, 126.88, 127.96, 128.05, 128.97, 131.21, 132.10, 133.06, 149.22, 152.10, 162.48, 167.84 ppm.

3.3.5 2-Phenyl-4-(3'-Nitrophenylmethyidene)-5-Oxazolinone (3e): [49]

IR (KBr): ν C=O 1787.89 cm-1.

1H NMR (400 MHz, CDCl3): δ 7.41 (s, 1H, =C-H), 7.50–7.95 (m, 5H, ArH), 7.62 (t, 1H, H-5′), 7.84 (dd, 1H, H-6′), 8.19 (dd, 1H, H-4′), 8.54 (s, 1H, H-2′) ppm.

13C NMR (100 MHz, CDCl3): δ 121.7, 125.4, 127.6, 128.8, 129.1, 129.9, 131.8, 132.8, 134.3, 135.1, 141.8, 148.5, 160.9, 171.5 ppm.

MS (ESI) m/z: 294.06 [M+H] +•.

3.3.6 2-Phenyl-4-(2'-Nitrophenylmethylidene)-5-Oxazolinone (3f): [50]

IR (KBr): ν C=O 1793.68 cm-1.

1H NMR (300 MHz, CDCl3): δ 7.53–7.96 (m, 5H, Ar-H), 7.80–8.01 (m, 4H, Ar-H), 8.37 (s, 1H, =C-H) ppm.

13C NMR (100 MHz, CDCl3): δ 112.2, 123.2, 126.1, 127.1, 127.3, 128.0, 128.4, 128.5, 128.7, 128.9, 131.0, 131.1, 134.2, 147.3, 160.8, 165.9 ppm.

MS (ESI) m/z: 295.06 [M+H]; HRMS-EI: found: 294.064, calculated: 294.071.

3.3.7 2-Phenyl-4-(2'-Chlorophenylmethylidene)-5-Oxazolinone (3g): [50]

IR (KBr): ν C=O 1793.68 cm-1.

1H NMR (300 MHz, CDCl3): δ 7.51‒7.94 (m, 5H, Ar-H), 7.31‒7.43 (m, 4H, Ar-H), 7.63 (s, 1H, C=C-H) ppm.

13C NMR (100 MHz, CDCl3): δ 112.3, 126.0, 126.3, 127.3, 128.0, 128.3, 128.5, 128.8, 131.1, 131.3, 132.3, 133.5, 160.1, 168.9 ppm.

MS (ESI) m/z: 284.04 [M+H];

HRMS-EI: found: 283.040, calculated: 283.047.

3.3.8 2-Phenyl-4-(4'-Chlorophenylmethylidene)-5-Oxazolinone (3h):

IR (KBr): ν C=O 1795.6 cm-1.

1HMR (400 MHz, CDCl3): δ 7.37 (s, 1H, =C-H), 7.59–7.73 (m, 5H), 8.12 (d, 2H, J = 7.2 Hz), 8.31 (d, 2H, J = 8.2 Hz) ppm.

3.3.9 2-Phenyl-4-(2'-Furylmethylidene)-5-Oxazolinone (3i):

IR (KBr): ν C=O 1789.82 cm-1.

1HMR (400 MHz, CDCl3): δ 6.83 (d, 1H, J = 3.6 Hz), 7.27 (s, 1H, =C-H), 7.60–7.62 (m, 3H), 7.68 (d, 1H, J = 7.2 Hz), 8.08–8.11 (m, 3H) ppm.

3.3.10 2-Phenyl-4-(E-Styrylmethylidene)-5-Oxazolinone (3j):

IR (KBr): ν C=O 1785.96 cm-1.

1HMR (400 MHz, CDCl3): δ 6.709 (d, 2H, J = 12 Hz), 7.23 (d, 1H, J = 7.6 Hz, =C-H), 7.52–7.61 (m, 5H), 8.23–8.27 (m, 5H) ppm.

3.3.11 2-Phenyl-4-(4'-N,N-Dimethylaminophenylmethylidene)-5-Oxazolinone (3k): [49]

IR (KBr): ν C=O 1787.89 cm-1.

1H NMR (400 MHz, CDCl3): δ 2.98 (s, 6H, 2 × CH3), 6.64 (dd, 2H), 7.18 (dd, 2H), 7.36 (s, 1H, =C-H), 7.60–8.10 (m, 5H, ArH) ppm.

13C NMR (100 MHz, CDCl3): δ 44.1, 113.2, 126.8, 128.1, 128.9, 129.8, 131.2, 132.4, 134.8, 141.6, 151.7, 163.8, 175.3 ppm.

MS (ESI) m/z: 292.12 [M+H]+•.

4. Mechanism

In the present reaction, hippuric acid gets activated by Zn (OCOCH3)2 followed by conjugate addition of I across the carbonyl carbon of the aldehyde takes place to give intermediate II, which reacts with a molecule of acetic anhydride and loses two molecules of acetic acid to give the intermediate III. In the final step the loss of two more molecules of acetic acid from III in the presence of another molecule of acetic anhydride may occur to give the product IV. The last two steps are important, and we feel that, ultrasound is responsible for enhancing the rate as shown in the Scheme 2.

Click to view original image

Scheme 2 Mechanism of formation of 2-phenyl-4-arylmethylidene-5-oxazolinones.

5. Conclusion

In conclusion, an ultrasound-assisted, highly economical, energy-efficient method for the preparation of biologically important oxazoline-5-one derivatives by the condensation of hippuric acid with aryl aldehydes/furfural/cinnamaldehyde in acetic anhydride/EtOH and Zn(OCOCH3)2·2H2O as a catalyst has been developed. The present method is efficient and simple, high yield, short duration and ease of workup make the method advantageous. Most importantly, the crude product quality is high enough that, in some cases, further purification is not required.

Acknowledgments

Dr. Sadeq Hamood Saleh Azzam sincerely thanks the Department of Chemistry, Sana’a University, Sana’a, YEMEN for providing research facility. Dr. Mohamed Afzal Pasha acknowledges the University Grants Commission, New Delhi, INDIA for BSR Faculty Fellowship: No. F.18-1/2011 (BSR); November, 2019.

Author Contributions

Dr. Sadeq Hamood Saled Azzam prepared the oxazoline-5-ones and characterized them and prepared the draft of the manuscript. Ms. Amreen Khanum repeated the synthesis of oxazoline-5-ones as per the reviewers suggestions, characterized them and updated the references. Prof. Mohamed Afzal Pasha is the corresponding author, Research supervisor, corrected and edited the manuscript and Guided both the coauthors.

Competing Interests

The authors have declared that no competing interests exist.

Additional Materials

The following additional materials are uploaded at the page of this paper.

1. Supplementary.

References

  1. Cleary T, Rawalpally T, Kennedy N, Chavez F. Catalyzing the Erlenmeyer Pӧlchl reaction: Organic bases versus sodium acetate. Tetrahedron Lett. 2010; 51: 1533-1536. [CrossRef]
  2. Anandgaonker P, Kulkarni G, Gaikwad S, Rajbhoj A. Nanocrystalline titanium dioxide catalyst for the synthesis azlactones. Chinese J Cat. 2014; 35: 196-200. [CrossRef]
  3. Tandel RC, Manmen D. Synthesis and study of some compounds containing oxazolone ring, sowing biological activity. Indian J Chem. 2008; 47B: 932-937. [CrossRef]
  4. Moxley RT, Ashwal S, Pandya S, Connolly A, Florence J, Mathews K, et al. Practice parameter: Corticosteroid treatment of Duchenne dystrophy. Neurology. 2005; 64: 13-20. [CrossRef]
  5. Lesieur A, Aichew H. Eur. Patent 390: 673, 03, 1990. Chem Abstr. 1991; 114: 143.
  6. Vingar SK, Bobade AS, Khadse BG. Synthesis and antimicrobial activity of 6-chlorocinnolinothiazoles. Indian J Heterocycl Chem. 2001; 11: 35-38.
  7. Benedetti-Doctorovich V, Burgess EM, Lambropoulos J, Lednicer D, Van Derveer D, Zalkow LH.Synthesis of 2-methyl-(Z)-4-(phenylimino)naphth[2,3-d]oxazol-9-one, a monoimine quinone with selective cytotoxicity toward cancer cells. J Med Chem. 1994; 37: 710-712. [CrossRef]
  8. Pereira ER, Sancelma M, Voldoire A, Prudhomme M. Synthesis and antimicrobial activities of 3-N-substituted-4,5-bis(3-indolyl)oxazol-2-ones. Bioorg Med Chem Lett. 1997; 7:2503-2506. [CrossRef]
  9. Viti G, Namnicine R, Ricci R, Pestelline V, Abeli L, Furio M. New antagonists of platelet-activating factor containing 2-oxazolidinone or 2-morpholinone. Eur J Med Chem. 1994; 29: 401-406. [CrossRef]
  10. Moise M, Sunel V, Profire L, Popa M, Desbrieres J, Peptu C. Synthesis and biologicalactivity of some new 1,3,4-thiadiazole and 1,2,4-triazole compounds containing a phenylalanine moiety. Molecules. 2009; 14: 2621-2631. [CrossRef]
  11. Faroumadi A, Mirzaei M, Shafiee A. Antituberculosis agents, I:Synthesis and antituberculosis activity of 2-aryl-1,3,4-thiadiazole derivatives. Pharmazie. 2001;56: 610-612. [CrossRef]
  12. Mamolo MG, Falagiani V, Zanpier D, Vio L, Banfi E. Synthesis and antimycobacterial activity of [5-(pyridin-2-yl)-1,3,4-thiadiazol-2-ylthio]acetic acid arylidene-hydrazide derivatives. Farmaco. 2001; 56: 587-592. [CrossRef]
  13. Zamani K, Faghifi K, Tofighi T, Shariatzadeh MR. Synthesis and antimicrobial activity of some pyridyl and naphthyl substituted 1,2,4-triazole and 1,3,4-thiadiazole derivatives. Turk J Chem. 2004; 28: 95-100.
  14. Clerici F, Pocar D, Guido M, Loche A, Perlini V, Brufani M. Synthesis of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives and evaluation of their antidepressant and anxiolytic activity. J Med Chem. 2001; 44: 931-936. [CrossRef]
  15. Yeh VSC. Recent advances in the total synthesis of oxazole-containing natural products.Tetrahedron. 2004; 60: 52: 11995-12042. [CrossRef]
  16. Hamada Y, Shioiri T. Recent progress of the synthetic studies of biologically active marine cyclic peptides and depsipeptides. Chem Rev. 2005; 105: 4441-4482. [CrossRef]
  17. Dabholkar VV, Parab SD. Synthesis of novel triazole, quinoline, oxazole and imidazole annulated carbostyrils by microwave irradiation. Indian J Chem. 2007; 46B: 344-348. [CrossRef]
  18. Dabholkar VV, Mishra SKJ. Microwave-mediated synthesis of some novel heterocycles containing thiazole, oxazole, thiazine, oxazine, thiadiazine and triazolo-thiadiazine moiety. Indian J Chem. 2006; 45B: 2112-2117. [CrossRef]
  19. Beccalli EM, Clerici F, Gelmi ML. 5 (4H)-oxazolones. Part XIII. A new synthesis of 4-ylidene-5(H)-oxazolones by the Stille reaction. Tetrahedron. 1999; 55: 781-786. [CrossRef]
  20. Zhou B, Chen W. The zwitterionic imidazolium salt: First used for synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones under solvent-free conditions. J Chem. 2013; 2013: 280585. [CrossRef]
  21. Yu C, Zhou B, Su W, Xu Z. Erlenmeyer synthesis for azlactones catalyzed by ytterbium (III) triflate under solvent-free conditions. SynthCommun. 2006; 36: 3447-3453. [CrossRef]
  22. Pattarawarapan M, Jaita S, Phakhodee W. A convenient synthesis of 4-arylidene-2-phenyl-5(H)-oxazolones under solvent-assisted grinding. Tetrahedron Lett. 2016; 57: 3171-3174. [CrossRef]
  23. Moghanian H, Shabanian M, Jafari H. Microwave-assisted efficient synthesis of azlactone derivatives using TsCl/DMF under solvent-free conditions. C R Chim. 2012; 15: 346-349. [CrossRef]
  24. Mobinikhaledi A, Moghanian H, Pakdel S. Microwave-assisted efficient synthesis of azlactonederivatives using 2-aminopyridine-functionalized sphere SiO2 nanoparticles as a reusableheterogeneous catalyst. Chin Chem Lett. 2015;26: 557-563. [CrossRef]
  25. Puterová Z, Sterk H, Krutošíková A. Reaction of substituted furan-2-carboxaldehydes and furo[b]pyrrole type aldehydes with hippuric acid. Molecules. 2004;9: 11-21. [CrossRef]
  26. Karade NN, Shirodkar SG, Dhoot BM, Waghmare PB. Montmorillonite K-10 mediated erlenmeyer synthesis of 4-arylmethylene-2-phenyl-5(4H)-oxazolones. J Chem Res. 2005; 2005: 46-47. [CrossRef]
  27. Rostamizadeh N, Khajeh-Amiri A, Moghanian H. Microwave-assisted erlenmeyer synthesis of azlactones catalyzed by MgO/Al2O3 under solvent-free conditions. Synth React Inorg MetOrg Nano-Met Chem. 2016; 46: 631-634. [CrossRef]
  28. Wang Y, Shi D, Lu Z, Dai G. A convenient synthesis of 4-arylidene-2-phenyloxazol-5-ones catalyzed by KF-Alumina. Synth Commun. 2000;30: 707-712. [CrossRef]
  29. Romanelli G, Autino JC, Vázquez P, Pizzio L, Blanco M, CáCeres C. A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica-alumina supported heteropolyacids. Appl Catal A. 2009; 352: 208-213. [CrossRef]
  30. Ahmadi SJ, Sadjadi S, Hosseinpour M. A green protocol for Erlenmeyer-Plӧchl reaction by using iron oxide nanoparticles under ultrasonic irradiation. Ultrason Sonochem. 2013; 20: 408-412. [CrossRef]
  31. Paul S, Nanda P, Gupta R, Loupy A. Calcium acetate catalyzed synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones under solvent-free conditions. Tetrahedron Lett. 2004; 45: 425-427. [CrossRef]
  32. Khodaei MM, Khosropour AR, Jomor SJ. Efficient and chemoselective conversion of arylaldehydes to their azalactones catalyzed by Bi(III) salts under solventfree conditions. J Chem Res. 2003; 2003: 638-641. [CrossRef]
  33. Kurane R, Khanapure S, Kale D, Salunkhe R, Rashinkar G. An expedient synthesis of oxazolones using a cellulose supported ionic liquid phase catalyst. RSC Adv. 2016; 6: 44135-44144. [CrossRef]
  34. Rostami M, Khosropour A, Mirkhani V, Moghadam M, Tangestaninejad S, Mohammadpoor-Baltork I. Organic-inorganic hybrid polyoxometalates: Efficient, heterogeneous and reusable catalysts for solvent-free synthesis of azlactones. Appl Cata A. 2011; 397: 27-34. [CrossRef]
  35. Heravi MR. Erlenmeyer synthesis of azlactones by sonochemical reaction in ionic liquids. J Univ Chem Technol Metall. 2009; 44: 86-90.
  36. Sadjadi S, Sepehrian H. Cu(OAc)2/MCM-41: An efficient and solid acid catalyst forsynthesis of 2-arylbenzothiazoles under ultrasound irradiation. Ultrason Sonochem. 2011; 18: 480-483. [CrossRef]
  37. Reddy MBM, Pasha MA. Molecular iodine–catalyzed, mild, effective, ecofriendly, microwave-assisted, one-pot synthesis of 5-arylmethylidene-2-phenyloxazol-4-ones (azalactones) under solvent-free conditions. Synth Commun. 2010; 40: 1895-1898. [CrossRef]
  38. Azzam SHS, Chandrappa GT, Pasha MA. Sonochemical hot-spot assisted one-pot synthesis of 4-arylmethylidene-2-phenyl-4H-oxazol-5-ones using nano-MgO as an efficient catalyst. Lett Org Chem. 2013; 10:283-290. [CrossRef]
  39. Tabassum S, Govindaraju S, Pasha MA. Sonochemistry-an innovative opportunity towards a one-pot three-component synthesis of novel pyridylpiperazine derivatives catalysed by meglumine in water. New J Chem. 2017; 41: 3515-3523. [CrossRef]
  40. Govindaraju S, Tabassum S,Pasha MA. Silica iodide catalyzed, ultrasound-promoted, one-pot four-component synthesis of novel 1,4,5,6-tetrahydropyridine-3-carboxylate derivatives. Phosphorus Sulfur Silicon Relat Elem. 2017; 192: 292-299. [CrossRef]
  41. Govindaraju S, Tabassum S, Khan RU, Pasha MA. Catalyst-free green synthesis of novel2-amino-4-aryl-3-(4-fluorophenyl)-4,6,7,8-tetrahydroquinolin-5(1H)-ones via a one-pot four-component reaction under ultrasonic condition. Chem Heterocycl Compd. 2016; 52:964-969. [CrossRef]
  42. Tabassum S, Govindaraju S, Khan RR, Pasha MA. Ultrasound mediated, green innovation for the synthesis of polysubstituted-1,4-dihydropyridines. RSC Adv. 2016; 6: 29802-29810. [CrossRef]
  43. Sudha S, Pasha MA. Catalyst-free ultrasound assisted novel one pot pseudo five component synthesis of aryl-bis-[1H-pyrazol-5-ol-4-yl]methanes, het(aryl)-bis-[1H-pyrazol-5-ol-4-yl]methanes and their 1-phenyl derivatives in aqueous medium. Green Synth Catal. 2022; 3: 190-193. [CrossRef]
  44. Tabassum S, Santosh G, Khan RR, Pasha MA. Ultrasound mediated, iodine catalyzed green synthesis of novel 2-amino-3-cyano-4H-pyran derivatives. Ultrason Sonochem. 2015; 24: 1-7. [CrossRef]
  45. Siddekha A, Azzam SH, Pasha MA. Ultrasound-assisted one-pot four-component synthesis of 1,4,6,8-tetrahydroquinolines in aqueous medium. Synth Commun. 2014; 44:424-432. [CrossRef]
  46. Pasha MA, Nagashree S. Ni(NO3)2·6H2O/I2/water: A new, mild and efficient system for the selective oxidation of alcohols into aldehydes and ketones under sonic condition. Ultrason Sonochem. 2013; 20:810-814. [CrossRef]
  47. Datta B, Pasha MA. Silica chloride catalyzed efficient route to novel 1-amidoalkyl-2-naphthylamines under sonic condition in water. Ultrason Sonochem. 2013; 20:303-307. [CrossRef]
  48. Khandebharad AU, Kulkarni PS, Ubale PS, Dhotre BK, Kute PR, Sarda SR. Synergism of ultrasound and choline hydroxide for the synthesis of the azlactone derivatives. Polycycl Aromat Compd. 2022.doi: 10.1080/10406638.2022.2072913. [CrossRef]
  49. Parveen M, Ahmad F, Malla AM, Azaz S, Silva MR, Silva PSP. [Et3NH][HSO4]-mediated functionalization of hippuric acid: An unprecedented approach to 4-arylidene-2-phenyl-5(4H)-oxazolones. RSC Adv. 2015; 5: 52330-52346. [CrossRef]
  50. Jadhav SA, Sarkate AP, Farooqui M, Shinde DB. Greener approach: Ionic liquid [Et3NH][HSO4]-catalyzed multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)oxazolones under solvent-free condition. Synth Commun. 2017; 47: 1676-1683. [CrossRef]
Newsletter
Download PDF Supplementary File Download Citation
0 0

TOP