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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 |
Appears in Collections: | Journal Articles |
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