6533b832fe1ef96bd129ac5c
RESEARCH PRODUCT
Diels-Alder Reactions ofin situ generated N-benzoylindolo-2,3-quinodimethane with carbodienophiles
Ulf PindurManfred Habersubject
Indole testIn situDetection limitHplc analysischemistry.chemical_compoundchemistryDiels alderOrganic chemistryTetracyanoethyleneDivinyl sulfonedescription
The indolo-2,3-quinodimethane (5), generated from 2,3-bis(bromomethyl)indole (4), was trapped with unsymmetrical carbodienophiles or N, N′-p-phenylenedimaleimide to furnish the 1,2,3,4-tetrahydrocarbazoles (6–9). [4 + 2]-Cycloaddition of 5 with tetracyanoethylene gave rise to the tetracyanocarbazole (10) and a subsequent product 11a or 11b. The Diels-Alder reaction of 5 with divinyl sulfone was regiospecific within the detection limits of HPLC analysis. Similarly, the reaction of 5 with N, N′-p-phenylenedimaleimide yielded solely the stereoisomer 9.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1993-01-01 | Journal f�r Praktische Chemie/Chemiker-Zeitung |