Reactions of 2-aza-1,3,5-trienes with superbases: competition between formation of thiazoles and azepines

Reactions of 2-aza-1,3,5-trienes with superbases: competition between formation of thiazoles and azepines

For the case of 1-(allylsulfanyl)-2-methoxy- N -(1-methylethylidene)buta-1,3-dien-1-amine, obtained from α-lithiated methoxyallene, isopropyl isothiocyanate, and allyl bromide, it was shown that 5-ethylidene-2-(1-methoxyprop-2-enyl)-4,4-dimethyl-4,5-dihydro-1,3-thiazole and 6-methoxy-2-methyl-3H-aze...

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Veröffentlicht in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2012, Vol.47 (11), p.1430-1435
Hauptverfasser: Nedolya, N. A., Tarasova, O. A., Volostnykh, O. G., Albanov, A. I., Trofimov, B. A.
Format: Artikel
Sprache:eng
Schlagworte:
Bisphenol-A
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
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Zusammenfassung:For the case of 1-(allylsulfanyl)-2-methoxy- N -(1-methylethylidene)buta-1,3-dien-1-amine, obtained from α-lithiated methoxyallene, isopropyl isothiocyanate, and allyl bromide, it was shown that 5-ethylidene-2-(1-methoxyprop-2-enyl)-4,4-dimethyl-4,5-dihydro-1,3-thiazole and 6-methoxy-2-methyl-3H-azepine are formed competitively upon the action of the t-BuOK–THF–DMSO system.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-012-0930-5