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Please use this identifier to cite or link to this item: http://hdl.handle.net/2080/517

Title: A Pummerer-based generation and trapping of furo[3,4-c]pyridines: an approach to nitrogen containing heterocyclic analogues of 1-arylnaphthalene lignans
Authors: Sarkar, T K
Basak, S
Panda, Niranjan
Keywords: azaisobenzofuran
Pummerer rearrangement
Diels–Alder reaction
heterolignan
Issue Date: 2002
Publisher: Elsevier
Citation: Tetrahedron Letters, Vol 43, Iss 7, P 1341-1344
Abstract: The Pummerer reaction of o-benzoyl substituted pyridylmethyl sulfoxides generates α-thiocarbocations, the interception of which by the neighbouring keto functionality produces thio-substituted furo[3,4-c]pyridines as transient intermediates; the latter undergo [4+2] cycloaddition with an added dienophile. Base-induced ring opening of the cycloadducts followed by aromatization gives substituted isoquinolines related to heterocyclic analogues of 1-arylnaphthalene lignans.
Description: Copyright for this article belongs to Elsevier
URI: http://dx.doi.org/10.1016/S0040-4039(01)02379-6
http://hdl.handle.net/2080/517
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