REACTIONS OF CYCLIC OXALYL COMPOUNDS .38. NEW ISOINDIGOIDE DYES FROM HETEROCYCLIC 2,3-DIONES - SYNTHESIS AND THERMAL REARRANGEMENT

Authors
KOLLENZ G PENN G THEUER R FABIAN WMF ELNABI HAA ZHANG X PETERS K PETERS EM VONSCHNERING HG
Citation
G. Kollenz et al., REACTIONS OF CYCLIC OXALYL COMPOUNDS .38. NEW ISOINDIGOIDE DYES FROM HETEROCYCLIC 2,3-DIONES - SYNTHESIS AND THERMAL REARRANGEMENT, Tetrahedron, 52(15), 1996, pp. 5427-5440
Citations number
79
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
15
Year of publication
1996
Pages
5427 - 5440
Database
ISI
SICI code
0040-4020(1996)52:15<5427:ROCOC.>2.0.ZU;2-P
Abstract
The heterocyclic 2,3-diones 1 and 11 together with Lawesson reagent (L R) afford novel isoindigoide dyes 4 and 12, respectively. 4a can therm ally be isomerized into the pyrano[4,3-c]pyrane 6, accompanied by a si gnificant hypsochromic shift which,uas corroborated by quantum chemica l calculations. The phoshporanylidene derivative 13 was obtained via W ittig reaction of 1. All structural assignments were based on X-ray st udies of 4a and 13. Copyright (C) 1996 Elsevier Science Ltd