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A new tautomeric zwitterion form of 2-acylamino-4H-1,3,4-oxadiazino[5,6-b]quinoxalines in solution

✍ Scribed by Yoshihisa Kurasawa; Takako Mitomi; Yoshihisa Okamoto; Ho Sik Kim

Publisher
Journal of Heterocyclic Chemistry
Year
1998
Tongue
English
Weight
323 KB
Volume
35
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The reaction of 2‐acyiamino‐8‐chloro‐4‐methyl‐4__H__‐1,3,4‐oxadiazino[5,6‐b]quinoxalines 2a‐d with methyl iodide/base gave the 8‐chloro‐4,10‐dimethyl‐4__H__‐1,3,4‐oxadiazino[5,6‐b]quinoxalin‐10‐ium‐2‐acylamidates 4a‐d, respectively. Comparison of the nmr spectral data between compounds 2a‐d and 4a‐d in deuteriodimethyl sulfoxide or in deuteriotrifluoroacetic acid established that compounds 2a‐d existed as the zwitterionic tautomers 2′a‐d in solution.

📜 SIMILAR VOLUMES

Synthesis of 4H-1,3,4-oxadiazino[5,6-b]q
Synthesis of 4H-1,3,4-oxadiazino[5,6-b]quinoxalines from 2-substituted quinoxaline 4-oxides
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## Abstract The reaction of 6‐chloro‐2‐(1‐methylhydrazino)quinoxaline 4‐oxide 8 with acetic anhydride resulted in the intramolecular cyclization to give 8‐chloro‐2,4‐dimethyl‐4__H__‐1,3,4‐oxadiazino[5,6‐__b__]quinoxaline 7a, while the reaction of compound 8 with acetic anhydride/pyridine or acetic

A convenient synthesis of 2-amino-4H-1,3
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## Abstract The reaction of 6‐chloro‐2‐(1‐methylhydrazino)quinoxaline 4‐oxide 5 with a 2‐fold molar amount of ethyl chloroglyoxalate gave ethyl 8‐chloro‐4‐methyl‐4__H__‐1,3,4‐oxadiazino[5,6‐__b__]quinoxaline‐2‐carboxylate 6, whose reaction with hydrazine hydrate afforded the C~2~‐hydrazinocarbonyl

A selective synthesis of 2-arylamino-4H-
A selective synthesis of 2-arylamino-4H-1,3,4-thiadiazino[5,6-b]-quinoxalines and mesoionic triazolo[4,3-a]quinoxaline
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## Abstract The reaction of the 6‐chloro‐2‐(1‐methyl‐2‐thiocarbamoylhydrazino)quinoxaline 4‐oxides 3a‐d with trifluoroacetic anhydride gave the 2‐(__N__‐aryl)trifluoroacetamido‐8‐chloro‐4‐methyl‐4__H__‐1,3,4‐thiadiazino‐[5,6‐__b__]quinoxalines 7a‐d, respectively, while the reflux of compounds 3a‐c