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Selenium-containing heterocycles from Isoselenocyanates: Synthesis of 1H-5-Selena-1,3,6-triazaaceanthrylene derivatives


Atanassov, Plamen K; Linden, Anthony; Heimgartner, Heinz (2003). Selenium-containing heterocycles from Isoselenocyanates: Synthesis of 1H-5-Selena-1,3,6-triazaaceanthrylene derivatives. Helvetica Chimica Acta, 86(9):3235-3243.

Abstract

The reaction of aryl isoselenocyanates 8 with methyl 3-amino-4-chloro-1-ethylpyrrolo[3,2-c]quinoline-2-carboxylate (6) in boiling pyridine leads to tetracyclic selenaheterocycles of type 9 in high yield (Scheme 3). A reaction mechanism via an intermediate selenoureido derivative A and cyclization via nucleophilic substitution of Cl by Se is proposed (Schemes 3 and 5). The reaction of 6 with 4-bromophenyl isothiocyanate yields the analogous thiaheterocycle 12 (Scheme 4). The molecular structures of 9c and 12 have been established by X-ray crystallography.

Abstract

The reaction of aryl isoselenocyanates 8 with methyl 3-amino-4-chloro-1-ethylpyrrolo[3,2-c]quinoline-2-carboxylate (6) in boiling pyridine leads to tetracyclic selenaheterocycles of type 9 in high yield (Scheme 3). A reaction mechanism via an intermediate selenoureido derivative A and cyclization via nucleophilic substitution of Cl by Se is proposed (Schemes 3 and 5). The reaction of 6 with 4-bromophenyl isothiocyanate yields the analogous thiaheterocycle 12 (Scheme 4). The molecular structures of 9c and 12 have been established by X-ray crystallography.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2003
Deposited On:19 Aug 2013 06:40
Last Modified:05 Apr 2016 16:55
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.200390263

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