Synthesis of Pharmaceutically Important Isoxazoles

Authors

  • Sanjeevan S. Gaikwad Department of Chemistry, Bhausaheb Birajdar Senior College, Balsur Tq. Omerga 413 606, Dist. Osmanabad, Maharashtra, INDIA

Keywords:

Naphthofuran, Pyridine, Chalcones, Isoxazoles

Abstract

2-acetylnaphtho [2,1-b] furan has been synthesized by literature (Stoermer & Schaffer) method. It is then converted in to a series of Chalcones on treatment with p-substituted aromatic aldehyde. (1a-f) by Claisen-Schmidt condensation. These chalcones on reaction with Br2 in presence of methanol and glacial acetic acid gave their dibromo derivative (2a-f). This product reacts with hydroxylamine hydrochloride in pyridine and methanol respectively to get isomeric isoxazoles (3a-f) and (4a-f). The antimicrobial screening showed that many of these synthesised compounds have good activity against bacteria and fungi.

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References

V.P. Vaidya, C.S. Shreedhara, M. Gopal, M.S. Shahabuddin and P.S. Shenoy (2003), Evaluation of some novel heterocyclic compound for antifertility, antiinflamatory and analgesic activity, Indian J. Pharm. Sci. 65(6),580.

V.P. Vaidya, K.M. Mahadevan and H.M. Vagdevi(2003), Synthesis of novel napththo[2,1-b]Furopyrimidine derivatives, Indian J. Chem. 42(B), 1931

G.K.Nagraja, M.N.Kumarswamy, V.P.Vaidya, K.M.Mahadevan (2006) Microwave assisted synthesis of naphtho[2,1-b]furan-1,3,4-benzotriazepines: A potent antimicrobial agent, ARKIVOC 10,211

H.M.Vagdevi, V.P.Vaidya, K.P.Latha, B-Padmashali (2006) Synthesis and pharmacological examination of some thiazolidinone derivatives of naphtho(2,1-b)furan, Indian J. Pharm. Sci. 68,719

B. Padmshali, V.P. Vaidya, K.M. Mahadevan, K.P. Latha(2005) Synthesis of novel angularity fused pentacyclic heterocycles of pharmacological interest. Indian J. Chem. 44 (B), 1446

Y.Lee, S.M.Park and B.H.Kim(2009) Synthesis of-5-isoxazole-5-yl 21-deoxyuridine exhibiting antiviral activity against HSV and several RNA viruses, Bioorg.med.chem.lett.19,1126-1128.

M.P.Basappa, K.Sadashiva, S.Mantelingu, S.Nanjunda, K.S.Rangappa(2003), Solution-phase Synthesis of novel Δ2-isoxazoline libraries via 1,3-dipolar cycloaddition and their antifungal properties, Bioorg. Med. Chem. Lett. 11,21,4539-4544.

M.Zia, S.Hameed, I Ahmad, N.Tabassum, S.Yousuf(2020), Regino-isomeric isoxazole,sulfonates: Synthesis, characterization, electrochemical studies and DNA binding activity, J.Mole.Structure,1220,128635

S.S.Thakare, A.G.Doshi(2001), A novel synthesis of some isomeric isoxazoles, Asian J. of Chem.13(2)780-782

L.Chen, Z.Wang, H.Lin, Xinyne Li&B.Wang(2022), Tert. Butyl nitrite triggered radical cascade reaction for synthesizing isooxazoles by a one pot multicomponent strategy, Chem.Commun.58,9152-9155.

R.G.Micetich(1970), Studies in isoxazole chemistry. IV Isoxazoles via isoxazolines. Canadian J.Chem.,48,3753.

R.P.Barncs and A.Brandon (1943), The properties of p-methoxydibenzoylmethane, J.am. Chem. Soc. 65,1070-1072

A.Shaik, R.R.Bhandare, K.Palleapati, S.Nissan Kararao, V.Kancharlapalli, S.Shaik(2020), Antimicrobial,antioxidant and anticancer activities of some novel isoxazole ring containing chalcone and dihydropyrazole derivatives, molecules 25(5),1047

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Published

2019-03-30

How to Cite

Sanjeevan S. Gaikwad. (2019). Synthesis of Pharmaceutically Important Isoxazoles. International Journal for Research in Applied Sciences and Biotechnology, 6(2), 27–30. Retrieved from https://ijrasb.com/index.php/ijrasb/article/view/422

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