Nucleophilic addition reactions of 2-nitro-1-(phenylsulfonyl)indole. A newsynthesis of 3-substituted-2-nitroindoles

Authors
Pelkey, ET Barden, TC Gribble, GW
Citation
Et. Pelkey et al., Nucleophilic addition reactions of 2-nitro-1-(phenylsulfonyl)indole. A newsynthesis of 3-substituted-2-nitroindoles, TETRAHEDR L, 40(43), 1999, pp. 7615-7619
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
43
Year of publication
1999
Pages
7615 - 7619
Database
ISI
SICI code
0040-4039(19991022)40:43<7615:NARO2A>2.0.ZU;2-8
Abstract
2-Nitro-1 -(phenylsulfonyl)indole (1) undergoes nucleophilic addition react ions with the enolates of diethyl malonate and cyclohexanone, lithium dimet hylcuprate, and indole anion to afford the corresponding 3-substituted-2-ni troindoles (4-6, 8, 9) in low to high yields. Reaction of 1-(phenylsulfonyl )-2-(trialkylstannyl)indoles 13 and 14 with tetranitromethane affords the n ovel isoxazolo[5,4-b]indole 15 via a 1,3-dipolar cycloaddition reaction wit h in situ generated nitro formonitrile oxide (19). (C) 1999 Elsevier Scienc e Ltd. All rights reserved.