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Efficient Synthesis of Pyrroles from Chemoselective Addition of Primary Amines to 1,6-Dioxo-2,4-dienes

โœ Scribed by Ong, Chi Wi; Chen, Chong Meng; Wang, Long Hu; Jan, Jiing Jyh; Shieh, Po Chuen


Book ID
127155488
Publisher
American Chemical Society
Year
1998
Tongue
English
Weight
48 KB
Volume
63
Category
Article
ISSN
0022-3263

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Reaction of 1,6-dioxo-2,4-diene with P,Ss and Lawesson's reagent affords the 2,5-disubstituted thiophene. This reaction can take place regioselectively in the presence of BF~-etherate catalysis, useful for the synthesis of arylthiophene.

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## Abstract A oneโ€pot synthesis of dialkyl 1,3a,4,8bโ€tetrahydroโ€3a,8bโ€dihydroxyโ€1โ€alkylโ€4โ€oxoindeno[1,2โ€__b__]pyrroleโ€2,3โ€dicarboxylates __via__ threeโ€component reaction from indanโ€1,2,3โ€trione hydrate (ninhydrin), primary amines, and dialkyl acetylenedicarboxylates is described.