Intramolecular Diels—Alder reaction of 4-(N-furfuryl)aminobut-1-enes. New approach to the synthesis of 6,8a-epoxyoctahydroisoquinoline (3-aza-11-oxatricyclo[6.2.1.01,6]undec-9-ene) derivatives

Autor:	Alexey V. Varlamov, K. F. Turchin, Roman S. Borisov, A. A. Safronova, Fedor I. Zubkov, Eugeniya V. Nikitina
Rok vydání:	2004
Předmět:	Nitrogen atom Chemistry Intramolecular force General Chemistry Medicinal chemistry Cycloaddition Ene reaction Diels–Alder reaction
Zdroj:	Russian Chemical Bulletin. 53:860-872
ISSN:	1066-5285
Popis:	The intramolecular Diels—Alder reaction of readily accessible 4-substituted 4-(N-furfuryl)aminobut-1-enes was studied and a new one-step method was developed for the synthesis of 6,8a-epoxy-1,2,3,4,4a,5,6,8a-octahydroisoquinoline (3-aza-11-oxatricyclo[6.2.1.01,6]undec-9-ene) derivatives. The [4+2]-cycloaddition proceeds stereoselectively to form exo-adducts. The influence of substituents at the nitrogen atom in 4-(N-furfuryl)aminobut-1-enes on the cycloaddition pathway was examined.
Databáze:	OpenAIRE
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