Unusual formation of sterically hindered primary amines in a series of pyrrolo- and pyrido[1,2-a]indoles

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Title:Unusual formation of sterically hindered primary amines in a series of pyrrolo- and pyrido[1,2-a]indoles
Creators:
Jirkovsky, Ivo
Greenblatt, Lynne
Baudy, Reinhardt
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 11, pp. 2278-2287

Abstract

2,3-Dihydro-2,2,9-trimethyl-1<i>H</i>-pyrrolo[1,2-<i>a</i>]indol-1-amine and its 1-(1-pyrrolidinyl) analog have been synthesized from the corresponding 1-ol via mesylation in pyridine followed by treatment with pyrrolidine. Mechanisms of the former, unexpected amination are briefly discussed. Evidence is presented that the pyridine ring serves as a masked amino group. The phenomenon is partly attributed to steric congestion. Similar preparation of 2-bromo-6,7,8,9-tetrahydro-8,8,10-trimethylpyridol[1,2-<i>a</i>]indol-9-amine supports this notion.

Title:Unusual formation of sterically hindered primary amines in a series of pyrrolo- and pyrido[1,2-a]indoles
Creators:
Jirkovsky, Ivo
Greenblatt, Lynne
Baudy, Reinhardt
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:11
Page Range:pp. 2278-2287
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19912278UNSPECIFIED
ID Code:5157
Item Type:Article
Deposited On:22 Feb 2010 11:32
Last Modified:22 Feb 2010 10:32

Citation

Jirkovsky, Ivo; Greenblatt, Lynne; Baudy, Reinhardt (1991) Unusual formation of sterically hindered primary amines in a series of pyrrolo- and pyrido[1,2-a]indoles. Collection of Czechoslovak Chemical Communications, 56 (11). pp. 2278-2287. ISSN 0010-0765

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