S. Khanapure, E. Biehl
Mar 1, 1990
Citations
0
Influential Citations
22
Citations
Journal
Journal of Organic Chemistry
Abstract
Herein, we report the extension of the arynic isochroman-3-one synthesis to the preparation of 4-alkyl and 4-aryl derivatives of 6-methoxy-, 6,7-dimethoxy-, and 6,7-(methylenedioxy)isochroman-3-ones. The synthetic methodology consists of first treating bromo (methoxymethyl)arenes 3, 7, and 8 with lithioalkyl- or lithioarylacetonitriles under aryne-forming conditions (LDA/THF). Hydrolysis of the ortho α-cyano(methoxymethyl)arenes 10, 14, and 16, respectively, gives the corresponding isochroman-3-ones