3-Vinylcoumarins and 3-Vinylchromenes as Dienes. Application to the Synthesis of 3,4-Fused Coumarins and Chromenes

Toru Minami, Yasuyuki Matsumoto, Seigo Nakamura, Shinichiro Koyanagi, Masahiko Yamaguchi

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

The reaction of α-(diethylphosphono)-γ-butyrolactones 1 with o-hydroxyaryl aldehydes 2 and 7 gave 3-(2-hydroxyethyl)coumarins 3 in excellent yields. Treatment of 3 or 3-(2-hydroxyethyl)-2,2-dimethylchromenes 11 derived from 3 with triphenylphosphine dibromide led to the corresponding 3-(2-bromoethyl)coumarins 8 or 3-(2-bromoethyl)chromenes 12 in good yields. The Diels-Alder reaction of the 3-vinylcoumarins 13 or the 3-vinylchromenes 31, generated in situ from treatment of the bromides 8 or 12 with DBU, with a variety of dienophiles 14-19 and 35 produced regiospecific [2 + 4] cycloadducts, 3,4-fused coumarins 20-28 or 3,4-fused chromenes 32-34 and 36 in good to moderate yields.

Original languageEnglish
Pages (from-to)167-173
Number of pages7
JournalJournal of Organic Chemistry
Volume57
Issue number1
DOIs
Publication statusPublished - 1992 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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