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Diels-Alder Reactions of in situ generated N-benzoylindolo-2,3-quinodimethane with carbodienophiles (1993)

Pindur, U. ; Haber, Manfred

New York, NY : Wiley-Blackwell

Journal für Praktische Chemie/Chemiker-Zeitung 335 (1993), S. 12-16

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ISSN: 0941-1216

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 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.

Additional Material: 2 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/prac.19933350103

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