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4-(phenylsulfonyl)-4H-furo[3,4-b]indole - A stable synthetic analogue of indole-2,3-quinodimethane

โœ Scribed by Mark G. Saulnier; Gordon W. Gribble

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
237 KB
Volume
24
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The N-phenylsulfonyl derivative (2) of the previously unknown fused heterocycle 4Hfuro[3,4-blindole is synthesized from indole-3-carboxaldehyde (2) in 28% yield and undergoes a Diels-Alder reaction with benzyne to give 5H-benzo[b]carbazole (11) in -33% yield after deoxygenation and deprotection.

๐Ÿ“œ SIMILAR VOLUMES

2-Benzyl-4-(phenylsulfonyl)-1,2,3,4-tetr
2-Benzyl-4-(phenylsulfonyl)-1,2,3,4-tetrahydropyrrolo[3,4-b]indole
โœ Kishbaugh, Tara L. S. ;Gribble, Gordon W. ;Jasinski, Jerry P. ๐Ÿ“‚ Article ๐Ÿ“… 2007 ๐Ÿ› International Union of Crystallography ๐ŸŒ English โš– 798 KB

The indole and pyrrolidine ring systems of the title compound, C 23 H 20 N 2 O 2 S, are essentially coplanar. The angle between the planes of the phenylsulfonyl group and the indole ring system is 77.0 (1) . The benzyl ring and the pyrroloindole plane are nearly perpendicular, with an angle between

2-(4-Methoxybenzyl)-4-(phenylsulfonyl)-1
2-(4-Methoxybenzyl)-4-(phenylsulfonyl)-1,2,3,4-tetrahydropyrrolo[3,4-b]indole
โœ Kishbaugh, Tara L. S. ;Gribble, Gordon W. ;Jasinski, Jerry P. ๐Ÿ“‚ Article ๐Ÿ“… 2007 ๐Ÿ› International Union of Crystallography ๐ŸŒ English โš– 735 KB

The indole and pyrrolidine ring systems of the title compound, C 24 H 22 N 2 O 3 S, are essentially coplanar. The angle between the planes of the phenylsulfonyl group and the indole ring system is 89.1 (2) , which is characteristic of 1-(phenylsulfonyl)indoles. The benzyl ring is nearly perpendicula