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Solution and Solid‐Phase Synthesis of Functionalized 3‐Arylbenzofurans by a Novel Cyclofragmentation – Release Pathway
Author(s) -
Nicolaou K. C.,
Snyder Scott A.,
Bigot Antony,
Pfefferkorn Jeffrey A.
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(20000317)39:6<1093::aid-anie1093>3.0.co;2-s
Subject(s) - steric effects , alkoxide , chemistry , combinatorial chemistry , solid phase synthesis , cascade , polar effect , stereochemistry , organic chemistry , catalysis , biochemistry , peptide , chromatography
A diverse family of arylbenzofurans can be generated both in solution and on solid support from a novel reaction cascade starting from 2‐hydroxybenzophenones. The key step is a 5‐ exo ‐trig cyclization to generate alkoxide intermediates, which collapse to form the 3‐arylbenzofuran products (see scheme), an important class of compounds in biology and medicine. Not only are electron‐donating and electron‐withdrawing groups tolerated in the reaction, but pyridyl, naphthyl, and sterically hindered xylene analogues can also be obtained.