DSpace@nitr >
National Institue of Technology- Rourkela >
Journal Articles >

Please use this identifier to cite or link to this item: http://hdl.handle.net/2080/515

Title: A Sequential Pummerer-Diels-Alder Route for the Generation and Trapping of Furo[3,4-c]pyridines: Synthesis of Heterocyclic Analogues of 1-Arylnaphthalene Lignans
Authors: Sarkar, T K
Panda, Niranjan
Basak, S
Issue Date: 2003
Publisher: American Chemical Society
Citation: Journal of Organic Chemistry, Vol 68, Iss 18, P 6919-6927
Abstract: The Pummerer reaction of an o-benzoyl-substituted pyridylmethyl sulfoxide generates an -thiocarbocation, the interception of which by a neighboring keto functionality produces an -thio-substituted furo[3,4-c]pyridine as transient intermediate; the latter undergoes a Diels-Alder cycloaddition with an added dienophile. Base-induced ring opening of the cycloadduct followed by aromatization gives an isoquinoline derivative that may be looked upon as a heterocyclic analogue of 1-arylnaphthalene lignans. This procedure occurs readily with electron-poor dienophiles and the entire sequence can be run in one pot. The facility of the sequential Pummerer-Diels-Alder reaction hinges on the experimental conditions, the best results being obtained with heptafluorobutyric anhydride as the triggering agent in toluene containing a catalytic amount of p-toluenesulfonic acid. In the absence of a dienophile it is possible to isolate and characterize a rather unstable furo[3,4-c]pyridine derivative. An int...
Description: Copyright for the published version belongs to American Chemical Society
URI: http://dx.doi.org/10.1021/jo0344081 S0022-3263(03)04408-6
http://hdl.handle.net/2080/515
Appears in Collections:Journal Articles

Files in This Item:

File Description SizeFormat
niranjanACS.pdf24KbAdobe PDFView/Open

Show full item record

All items in DSpace are protected by copyright, with all rights reserved.

 

Powered by DSpace Feedback