Sequential Diels - Alder reaction of in situ generated 2,3-dimethylenepyrrole and carbodienophiles: Rapid synthesis of 2,3,6,7-tetrasubstituted carbazoles

Organic Letters

Volumn 2, Issue 1, 2000, Pages 73-76

  Vessels, Jeffrey T ^a   Janicki, Slawomir Z ^a   Petillo, Peter A ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

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[No Author keywords available]

Indexed keywords

EID: 0004412004     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991220o     Document Type: Article

References (50)

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26. There is a report of 9-acetylcarbazole-2,3,6,7-tetracarboxylic acid 2,3;6,7-dianhydride. However, the preparation and characterization of this compound was not reported. Kampar, V. E.; Mazere, I. V.; Meirovits, I. A.; Neiland, O. Y. Chem. Heterocycl. Compd. 1979, 15, 153-155.
27. 6 405.1204, found 405.1212.
28. 1H NMR.
29. Diels - Alder reactions with in situ generated 2.3-dimethylenepyrroles and dienophiles for the generation of 4,5-carbodisubstituted-2,3,4,5-tetrahydroindoles. Chou, T.; Chans, R. J. Chem. Soc., Chem. Commun. 1992, 549-551.
30. Diels - Alder reactions have been reported with in situ generated indole-2.3-quinodimethanes for the generation of 2,3-carbodisubstituted-1,2,3,4-tetrahydrocarbazoles. (a) Gallagher, T.; Maanus, P. Tetrahedron 1981 37, 3889-3897.
31. (b) Marinelli, E. R. Tetrahedron Lett. 1982, 23, 2745-2748.
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38. ○) was refluxed in a dry round-bottom flask fitted with an air-cooled reflux condenser under Ar until all of 1 was consumed. The solution was cooled, and the solvent was removed in vacuo.
39. Carbazole 3b was not observed in attempts to oxidize a mixture of 2b and 2c with DDQ.
40. 6 397.0586, found 397.0581.
41. The formation of 2a, 2b, 2c, and 2d are stereospecific and arise from two sequential [4 + 2] cycloaddition reactions. When fumaronitrile is used as a dienophile, two diastereomers of 2i are observed that were not separated, and thus, the relative configurations of the nitriles were not determined. The transformation with ethyl maleate affords six diastereomers of 2e. We hypothesize that the 2e mixture arises from isomerization of the dienophile and/or epimerization of each cycloadduct.
42. 2 269.1415, found 296.1416.
43. 15N 209.1205, found 209.1210.
44. In an analogous reaction, Trahanovsky and Cassady isolated furanoradialene at -60°C via the flash vacuum pyrolysis of 3,4-bis-(acetoxyrnethyl)-2,5-dimethylfuran. Trahanovsky, W. S.; Cassady, T. J. J. Am. Chem. Soc. 1984, 106, 8197-8201.
45. The monoadduct 8a was isolated when the reaction was not allowed to go to completion.
46. 3 287, found 287.
47. Use of pyridine in the formation of 2d resulted in a reduction of the yield from 89% to 70%. Use of DBU and KHMDS resulted in the rapid decomposition of 1. The use of acids such as TsOH. maleic acid, or HCl resulted in the decomposition of 1.
48. Sauer, J.; Wuest, H.; Mielert, A. Chem. Ber. 1964, 97, 3183-3207.
49. 20
50. 12g