A convenient method for the preparation of 5-, 6- and 7-azaindoles and their derivatives

The directed ortho lithiation of 2-tert-butoxycarbonylamino-3-methylpyridine (6 a) has provided a convenient method for the preparation of 1H-pyrrolo[2,3-b]pyridine (4 a, 7-azaindole). This procedure has been used to prepare a range of 3-substituted 2-tert-butoxycarbonylaminopyridines 6, 2- and 3-su...

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Published inSynthesis (Stuttgart) no. 7; pp. 877 - 883
Main Authors Hands, D, Bishop, B, Cameron, M, Edwards, JS, Cottrell, IF, Wright, SHB
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.07.1996
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORTHO LITHIATION
ORTHO FUNCTIONALIZATION
PYRROLOPYRIDINES
3-substituted-2-amino-pyridines
AMINES
5-, 6- and 7-azaindoles
directed ortho metallation
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Summary:The directed ortho lithiation of 2-tert-butoxycarbonylamino-3-methylpyridine (6 a) has provided a convenient method for the preparation of 1H-pyrrolo[2,3-b]pyridine (4 a, 7-azaindole). This procedure has been used to prepare a range of 3-substituted 2-tert-butoxycarbonylaminopyridines 6, 2- and 3-substituted and 2,3-disubstituted 1H-pyrrolo[2,3-b]pyridines 4 and shown to be of value in the preparation of 1H-pyrrolo[3,2-c]pyridine (15, 5-azaindole) and 1H-pyrrolo[2,3-c]pyridine (18, 6-azaindole) and derivatives.
ISSN:0039-7881
DOI:10.1055/s-1996-4312