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Please use this identifier to cite or link to this item: http://hdl.handle.net/2080/516

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contributor.authorSarkar, T K-
contributor.authorHazra, A-
contributor.authorGangopadhyay, P-
contributor.authorPanda, Niranjan-
contributor.authorSlanina, Z-
contributor.authorChun-Cheng, Lin-
contributor.authorHui-Ting, Chen-
identifier.citationTetrahedron, Vol 61, Iss 5, P 1155-1165en
descriptionCopyright for the published version belongs to Elsevieren
description.abstractAn aza-ene reaction has been used for the first time for the synthesis of two 5-membered lactam-hydrazides, each with a built-in allylsilane terminator for further elaboration. One of the lactam-hydrazides was transformed via an allylsilane-hydrazonium ion ring closure to a fused tetrahydropyrazole which may be considered as a mono-nitrogen analog of the biologically significant necine bases. A density functional theoretical study (B3LYP/6-21G*) was undertaken to provide insight into the factors that favor a synclinal transition structure of the hydrazonium ion intermediate leading to the tetrahydropyrazole. This stereocontrolled synthesis served as a model for the multi-step conversion of the other lactam-hydrazide, the substituted 2-pyrrolidinone, to necine bases (±)-supinidine and (±)-macronecine. An allylsilane-aldehyde ring closure formed the key step in the synthesis of these natural products.en
format.extent1013818 bytes-
subjectAza-ene reactionen
subjectHeterocyclic allylsilanesen
subjectFused tetrahydropyrazoleen
subjectNecine basesen
titleSynthesis of the necine bases (±)-macronecine and (±)-supinidine via an aza-ene reaction and allylsilane induced ring closureen
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