In:
Organic Chemistry Frontiers, Royal Society of Chemistry (RSC), Vol. 10, No. 7 ( 2023), p. 1780-1787
Abstract:
We report an atom-economical [4 + 4] cycloaddition of 2-alkynyl quinazolines with aza- ortho -quinone methides (ao-QMs) generated from 2-(bromomethyl)anilines to prepare various [1,5]diazocino[2,1- b ]quinazolinones in good to excellent yields in a short reaction time and under mild reaction conditions. Moreover, an estrone-derived [1,5] diazocino[2,1- b ]quinazolinone could be easily prepared in 30% total yield over five steps and biological assays reveal that the obtained [1,5] diazocino[2,1- b ] quinazolinones significantly inhibited nitric oxide generation in LPS-stimulated RAW264.7 cells. The present method features transition-metal free nature, broad substrate scope, good functional group tolerance, gram-scale preparation, and simple purification operation without flash column chromatography.
Type of Medium:
Online Resource
ISSN:
2052-4129
Language:
English
Publisher:
Royal Society of Chemistry (RSC)
Publication Date:
2023
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