In Situ Anionic Shielding for Regioselective Metalation: Directed peri and Iterative Metalation Routes to Polyfunctionalized 7??Azaindoles

C Schneider, E David, AA Toutov…

Index: Schneider, Cedric; David, Emilie; Toutov, Anton A.; Snieckus, Victor Angewandte Chemie - International Edition, 2012 , vol. 51, # 11 p. 2722 - 2726

Full Text: HTML

Citation Number: 22

Abstract

Herein we report on a) the unusual peri (C4)-metalation [1] reactivity of N-unprotected 7- azaindole 3-tertiary amide and 3-sulfonamide dianion frameworks (1, Figure 1) using the new concept of anionic shielding of C2 and its generalization for the synthesis of 4- substituted derivatives, b) the use of the thereby derived powerful directed metalation group (DMG) CONEt2 on C4 for the directed ortho metalation (DoM) of C5, thus leading, through ...