Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Quinoxaline Derivatives. VII. The Mechanism of the Formation of 6-Chloro-1,2,3,4,2′,3′-hexahydro-4,1′-dimethyl-3,2′-dioxoquinoxaline-2-spiro-3′-indole from a Quinoxaline N-Oxide Derivative by Nucleophilic Chlorination
Yusuf AhmadM. S. HabibM. IqbalM. I. QureshiZiauddin
Author information
JOURNALS FREE ACCESS

1965 Volume 38 Issue 10 Pages 1659-1663

Details
Abstract

The compound IVb named in the title has been obtained by an unambiguous route. It has been shown to be identical with the product of the reaction of the N-oxide (Ia) with ethanolic hydrogen chloride. Clark-Lewis and Katekar’s mechanism for the nucleophilic chlorination in the latter case has been discussed, and a modified mechanism proposed.
Isomeric 7-chloro-spiro-indole (IVc) has also been obtained by the rearrangement of the anilide IIIc. Similarly, the anilide IXi gives spiro-indole (IVc; H for Me’).
The anilides IIIb and IIIc give normal N-oxides Ib and Ic, which, with concentrated sulphuric acid, decompose and afford the amines IIb and IIc. IXi, instead of giving its N-oxide, yields 6-chloro-2,3-dihydroxyquinoxaline.

Information related to the author

This article cannot obtain the latest cited-by information.

© The Chemical Society of Japan
Previous article Next article
feedback
Top