A three-component, one-pot synthesis of 1,8-naphthyridine and isoxazole derivatives and computational elucidation of the mechanism

Guleli M., ERDEM S., Ocal N., Erden I., SARI Ö.

RESEARCH ON CHEMICAL INTERMEDIATES, vol.45, no.4, pp.2119-2134, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 45 Issue: 4
  • Publication Date: 2019
  • Doi Number: 10.1007/s11164-018-03721-z
  • Journal Name: RESEARCH ON CHEMICAL INTERMEDIATES
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2119-2134
  • Yıldız Technical University Affiliated: Yes

Abstract

An efficient and general method for the synthesis of substituted 3,4-dimethylisoxazolo[5,4-b]pyridine-5-carboxamide and benzo[b][1,8]naphthyridine-3-carboxamide derivatives by using 2,2,6-trimethyl-4H-1,3-dioxin-4-one, benzyl amine, aromatic aldehydes, 2-aminoquinoline, or 5-amino-3-methylisoxazole in the presence of a catalytic amount of p-toluenesulfonic acid or iodine is described. The formation of the products was investigated and the results obtained were also supported by theoretical calculations.