SYNTHESIS OF 2-NITROINDOLES VIA THE SUNDBERG INDOLE SYNTHESIS

Authors
PELKEY ET GRIBBLE GW
Citation
Et. Pelkey et Gw. Gribble, SYNTHESIS OF 2-NITROINDOLES VIA THE SUNDBERG INDOLE SYNTHESIS, Tetrahedron letters, 38(32), 1997, pp. 5603-5606
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
32
Year of publication
1997
Pages
5603 - 5606
Database
ISI
SICI code
0040-4039(1997)38:32<5603:SO2VTS>2.0.ZU;2-K
Abstract
A three-step sequence has been developed for converting o-nitrobenzald ehydes into 2-nitroindoles. The key step involves the thermolysis of 2 -(o-azidophenyl)nitroethylene (10) in xylenes which gives 2-nitroindol e (4) in 54% yield, akin to the classic Sundberg indole synthesis. Thi s procedure has also been utilized to synthesize 5,6-dimethoxy-2-nitro indole (14). (C) 1997 Elsevier Science Ltd.