N-Amination of Pyrrole and Indole Heterocycles with Monochloramine (NH2Cl)

A survey of several electrophilic ammonia reagents for the N-amination of indole- and pyrrole-containing heterocycles revealed that monochloramine (NH2Cl) is an excellent reagent for this transformation. Pyrroles and indoles containing a variety of substitution were aminated on nitrogen with isolate...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-02, Vol.69 (4), p.1368-1371
Main Authors: Hynes, John, Doubleday, Wendel W, Dyckman, Alaric J, Godfrey, Jollie D, Grosso, John A, Kiau, Susanne, Leftheris, Katerina
Format: Article
Language:English
Subjects:
Amination
Chemistry
Chloramines - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic Compounds - chemistry
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Indoles - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Pyrroles - chemistry
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Summary:A survey of several electrophilic ammonia reagents for the N-amination of indole- and pyrrole-containing heterocycles revealed that monochloramine (NH2Cl) is an excellent reagent for this transformation. Pyrroles and indoles containing a variety of substitution were aminated on nitrogen with isolated yields ranging from 45% to 97%.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo035587p