Tetrahedron letters

Surprising selectivity in the transformation of dimethoxy azaindoles

…, C Pathirana, J Castoro, N Soundararajan, A Staab

Index: Gesenberg, Kirsten; Deshpande, Prashant P.; Pullockaran, Annie; Xu, Feng; Wu, Dedong; Gao, Qi; Pathirana, Charles; Castoro, John; Soundararajan, Nachimuthu; Staab, Andrew Tetrahedron Letters, 2007 , vol. 48, # 15 p. 2675 - 2677

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Citation Number: 4

Abstract

Transformation of 4, 7-dimethoxy-6-azaindole into 4-hydroxy-7-methoxy-6-azaindole or 7- hydroxy-4-methoxy-6-azaindole can be readily controlled by careful selection of a reagent. Treatment with concentrated HCl results in hydrolysis at the 4-position exclusively, while TMS-I provides demethylation at the 7-position only. Products were unambiguously identified by single crystal X-ray crystallography.