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Synthesis of 1,3,5-triazineselones from imidoyl isoselenocyanates and amidines


Zhou, Y; Linden, A; Heimgartner, H (2012). Synthesis of 1,3,5-triazineselones from imidoyl isoselenocyanates and amidines. Heterocycles, 84(1):493-504.

Abstract

Whereas the reaction of N-phenylbenzimidoyl isoselenocyanate (1a) with N-phenylbenzamidine (5a) at room temperature gave the corresponding 1,3,5-triazine-2(1H)-selone (6a), the analogous reaction with the unsubstituted benzamidine (5b) led to di-1,3,5-triazin-2-yl diselenide (7b) via oxidative dimerization of the intermediate 1,3,5-triazine-2-selenol. In a similar manner, 1 and 2-amino-3,4,5,6-tetrahydropyridine (8) yielded the cyclohexa-1,3,5-triazine- 4-selone (9), which, in the presence of a strong base, reacted with a second molecule of isoselenocyanate to give the tricyclic 1,3,5-triazineselone (10). Finally, 2-amino-4,5-dihydro-1,3-thiazole (11) underwent the reaction with various isoselenocyanates (1) to yield 1,3-thiazolo[3,2-a][1,3,5]triazine-4-selones (12).

Abstract

Whereas the reaction of N-phenylbenzimidoyl isoselenocyanate (1a) with N-phenylbenzamidine (5a) at room temperature gave the corresponding 1,3,5-triazine-2(1H)-selone (6a), the analogous reaction with the unsubstituted benzamidine (5b) led to di-1,3,5-triazin-2-yl diselenide (7b) via oxidative dimerization of the intermediate 1,3,5-triazine-2-selenol. In a similar manner, 1 and 2-amino-3,4,5,6-tetrahydropyridine (8) yielded the cyclohexa-1,3,5-triazine- 4-selone (9), which, in the presence of a strong base, reacted with a second molecule of isoselenocyanate to give the tricyclic 1,3,5-triazineselone (10). Finally, 2-amino-4,5-dihydro-1,3-thiazole (11) underwent the reaction with various isoselenocyanates (1) to yield 1,3-thiazolo[3,2-a][1,3,5]triazine-4-selones (12).

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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:2012
Deposited On:14 Jan 2012 20:20
Last Modified:05 Apr 2016 15:18
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Dr. Helmut Legerlotz-Foundation, Zürich, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.3987/COM-11-S(P)9

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