Azatetralone synthesis via regioselective Grignard coupling and Parham cyclization

…, DE Fox, RC Friedmann, CW Murtiashaw

Index: Quallich, George J.; Fox, Darrell E.; Friedmann, Robert C.; Murtiashaw, C. William Journal of Organic Chemistry, 1992 , vol. 57, # 2 p. 761 - 764

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Citation Number: 34

Abstract

42, 3772. of 6 with Jones reagent gave the acid 9 (61%) as a colorless oil which solidified on standing. Intramolecular Parham cyclization was intended to conclude the azatetralone 15 synthesis. I2 Treatment of the acid 9 with n-butyllithium generated the azatetralone 15 in 12- 19% yield. Unreacted 9 was the major product obtained from the cyclization, the 3- protonated pyridine 13 was also isolated. During the Parham cyclization, it was observed ...