Synthesis of 2-heteroaryl-3-hydroxypyridines by ring expansion reactions of 2-acylfurans with ammonia
RWJ Chubb, MR Bryce, B Tarbit
Index: Chubb; Bryce; Tarbit Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 16 p. 1853 - 1854
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Citation Number: 17
Abstract
In the context of non-coupling routes to biaryls we were attracted to the work of Leditschke who reported in 1952 that 2-benzoylfuran (1, Het = Ph; R = H) reacted with ammonia to give 2-phenyl-3-hydroxypyridine. The proposed mechanism involves initial attack of ammonia at C-5 of the furan, leading to a ring opening–ring closure sequence, and the furan oxygen becomes the hydroxy group in the product. 9 Gruber extended this route to substituted phenyl ...
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