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Syntheses of 2‐Benzylbenzofuran Derivatives and 2‐Aryl‐nitrochroman Derivatives from Nitroalkene Precursors
Author(s) -
Huang ChiaYu,
Kuo ChunWei,
Kavala Veerababurao,
Yao ChingFa
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600314
Subject(s) - chemistry , dabco , nitro , alkene , aryl , octane , knoevenagel condensation , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , alkyl
Simple and straightforward methods for the synthesis of 2‐benzylbenzofuran, 3‐substituted 2‐benzylbenzofuran, and 2‐aryl‐nitrochroman derivatives are described. Benzofurans were generated from nitroalkenes by reduction with NaBH 4 followed by a Nef reaction and acid‐mediated cyclization, whereas 3‐substituted 2‐benzylbenzofurans were prepared from nitroalkenes by reactions with Grignard reagents followed by a Nef reaction and an acid‐mediated cyclization in a one‐pot process. The synthesis of chromans involved a Knoevenagel condensation and the 1,4‐diazabicyclo[2.2.2]octane (DABCO) assisted cyclization of β‐(2‐hydroxyphenyl)‐nitroethanes and benzaldehydes, also in a one‐pot process.