The Journal of Organic Chemistry

One-step synthesis of 3, 8-methano-1-aza [10] annulene derivatives via Diels-Alder reaction of benzocyclopropene with 1, 2, 4-triazines

JC Martin, JM Muchowski

Index: Martin, John C.; Muchowski, Joseph M. Journal of Organic Chemistry, 1984 , vol. 49, # 6 p. 1040 - 1043

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Citation Number: 14

Abstract

A new approach to the synthesis of 3, 8-methano-l-aza [101annulene derivatives based on the Diels-Alder reaction of benzocyclopropene with electron-deficient 1, 2, 4-triazines was developed. The exceptionally electron-deficient triazines 4a and 4b yielded azaannulenes 6a and 6b under normal conditions, while the less activated triazines 4c and 4d required ultrahigh pressure (15 kbar) to produce annulenes 6c and 6d. Both the disubstituted and ...