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A Pummerer-based generation and trapping of furo[3,4-c]pyridines: an approach to nitrogen containing heterocyclic analogues of 1-arylnaphthalene lignans

✍ Scribed by Tarun K Sarkar; Sankar Basak; Niranjan Panda

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
157 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

The Pummerer reaction of o-benzoyl substituted pyridylmethyl sulfoxides generates a-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.

📜 SIMILAR VOLUMES

ChemInform Abstract: Tandem Furo[3,4-b]p
ChemInform Abstract: Tandem Furo[3,4-b]pyridine Formation—Diels—Alder Reaction: An Approach to the Synthesis of Nitrogen Containing Heterocyclic Analogues of 1-Arylnaphthalene Lignans.
✍ Gouranga P. Jana; Binay K. Ghorai 📂 Article 📅 2008 🏛 John Wiley and Sons ⚖ 37 KB 👁 2 views

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