Synthesis of novel and diverse naphtho[1,2-b]furans by phosphine-catalyzed [3+2] annulation of activated 1,4-naphthoquinones and acetylenecarboxylates

Abstract

(ProQuest: ... denotes formulae and/or non-USASCII text omitted; see image)

A new phosphine-catalyzed [3+2] annulation reaction between activated 1,4-naphthoquinones and acetylenecarboxylates is described. This reaction provides a facile and efficient route to a variety of biologically promising and novel naphtho[1,2-......]furans. This devised method provides a first example for the synthesis of diverse naphtho[1,2-......]furan derivatives from 1,4-naphthoquinones via phosphine-catalyzed [3+2] annulation.

[Figure not available: see fulltext.]A variety of novel naphtho[1,2-......]furans were synthesized via the phosphine-catalyzed [3+2] annulation of activated 1,4-naphthoquinones and electron-deficient acetylenecarboxylates. In some reactions, both furannulation adducts and reductive/nucleophilic conjugate addition products were produced.