The Journal of Organic Chemistry

The direction of base-catalyzed aldol cyclization of 1, 5 diketones

S Danishefsky, A Zimmer

Index: Danishefsky,S.; Zimmer,A. Journal of Organic Chemistry, 1976 , vol. 41, p. 4059 - 4064

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Citation Number: 19

Abstract

A series of 1, s diketones of the type MeC (-O)(CH2) 3C (= O) CH2R (2) has been prepared. The route involves alkylation of 2, G-lutidine via its lithium salt with RX. The resultant pyridine, of the structure P-MeCsH:{N-fi-CH* R, is converted to the diketone of the type 2 by Birch-type reduction followed by hydrolysis. The base-catalyzed cyclodehydration of systems of the type 2 at room temperature has been examined in detail. The relative ...