Synthesis of Fused Six-Membered Lactams to Isoxazole and Isoxazoline by Sequential Ugi Four-Component Reaction and Intramolecular Nitrile Oxide Cyclization

Gülten Ş.

Journal of Chemical Education, vol.97, pp.3839-3846, 2020 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 97
  • Publication Date: 2020
  • Doi Number: 10.1021/acs.jchemed.9b01169
  • Journal Name: Journal of Chemical Education
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Applied Science & Technology Source, Chemical Abstracts Core, EBSCO Education Source, Education Abstracts, ERIC (Education Resources Information Center), MLA - Modern Language Association Database, Public Affairs Index, DIALNET
  • Page Numbers: pp.3839-3846
  • Çanakkale Onsekiz Mart University Affiliated: Yes

Abstract

Copyright © 2020 American Chemical Society and Division of Chemical Education, Inc.The advanced organic chemistry experiments describe the preparation of fused six-membered lactams to isoxazole and isoxazoline by employing Ugi four-component reaction (U-4CR) and intramolecular nitrile oxide cyclization (INOC) synthetic sequence. The experiments were carried out in 28 h (overnight for U-4CR) and 2 h (for INOC) using commercially available starting materials. The two-step reaction involves the in situ imine formation in the one-pot multicomponent reaction and in situ nitrile oxide formation in the INOC. The experiments are useful in the organic chemistry curriculum for the introduction of a one-pot multicomponent reaction and 1,3-dipolar cycloaddition reactions.