One-pot synthesis of functionalized indoles by cyclization of lithiated amides and nitriles with oxaldiimidoyl dichlorides

Authors
Langer, P Anders, JT Doring, M
Citation
P. Langer et al., One-pot synthesis of functionalized indoles by cyclization of lithiated amides and nitriles with oxaldiimidoyl dichlorides, EUR J ORG C, (20), 2001, pp. 3953-3959
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
20
Year of publication
2001
Pages
3953 - 3959
Database
ISI
SICI code
1434-193X(200110):20<3953:OSOFIB>2.0.ZU;2-5
Abstract
The reaction of the dianion of phenylacetonitrile with substituted oxalic a cid bis(imidoyl)chlorides resulted in the formation of 2-alkylidene-3-imino indoles, containing substituents at different positions of the heterocyclic nucleus. The cyclization of lithiated amides with bis(imidoyl) chlorides a fforded (3-imino-2,3-dihydro-1H-indol-2-ylidene) acetic amides. Excellent r egio- and E-diastereoselectivities were observed in all reactions.