One-pot and divergent synthesis of furo[3,2-c]quinolines and quinazolin-4(3H)-ones via sequential isocyanide-based three-component/Staudinger/aza-Wittig reaction

A new one-pot and divergent synthesis of multisubstituted furo[3,2-clquinolines and quinazolin-4(3H)-ones via sequential isocyanide-based three-component/Staudinger/aza-Wittig reactions was developed. The three-component reactions of dialkyl acetylenedicarboxylates, 2-azidobenzaldehydes (or 2-azidobenzoic acids) and isocyanides gave the azide intermediates, which were subsequently treated with triphenylphosphine to produce polysubstituted furo[3,2-clquinolines 6 or quinazolin-4(3H)-ones 10 in good overall yields by tandem Staudinger/aza-Wittig reactions. (C) 2020 Elsevier Ltd. All rights reserved.

Automated summary

A new one-pot and divergent synthesis of multisubstituted furo[3,2-cl]quinolines and quinazolin-4(3H)-ones was developed via sequential isocyanide-based three-component/Staudinger/aza-Wittig reactions, yielding good overall yields of the desired products.