SYNTHESIS AND DIELS-ALDER REACTION OF THIENO[2,3-C-4,5-C']DIPYRROLES

Authors
SHA CK TSOU CP
Citation
Ck. Sha et Cp. Tsou, SYNTHESIS AND DIELS-ALDER REACTION OF THIENO[2,3-C-4,5-C']DIPYRROLES, Tetrahedron, 49(31), 1993, pp. 6831-6836
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
31
Year of publication
1993
Pages
6831 - 6836
Database
ISI
SICI code
0040-4020(1993)49:31<6831:SADROT>2.0.ZU;2-2
Abstract
An efficient method for the synthesis of the thieno[2,3-c:4,5-c']dipyr role ring system is described. Reaction of 13 with sodium azide follow ed by the treatment with triphenylphosphine and water gave parent comp ound 4. Reaction of 13 with benzylamine or aniline afforded N,N'-disub stituted derivatives 15 and 16 respectively. Diels-Alder reaction of 1 5 with DMAD gave cycloadducts 17 and 18. Oxidative removal of the imin e bridge from 17 and 18 gave dibenzothiophene 19.