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13C-NMR study of 4H-1,3,4-thiadiazino[5,6-b]quinoxalines. A proof for the N5-deuteration in deuteriotrifluoroacetic acid

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

Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
202 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The carbon signals of the 2‐acylamino‐4__H__‐1,3,4‐thiadiazino[5,6‐b]quinoxalines 1a,b, 2‐acylamino‐4__H__‐1,3,4‐thiadiazino[5,6‐b]quinoxaline 1,1‐dioxides 2a,b, and 2‐amino‐4__H__‐1,3,4‐thiadiazino[5,6‐b]quinoxaline 3 in deuteriodimethyl sulfoxide and in deuteriotrifluoroacetic acid were assigned by the nmr (HMBC, HMQC) spectroscopy. The comparison of the carbon chemical shifts in deuteriodimethyl sulfoxide with those in deuteriotrifluoroacetic acid clarified that compounds 1a, 1b, and 3 were deuterized at the N~5~‐position in deuteriotrifluoroacetic acid, while the 1,1‐dioxides 2a,b did not undergo the N~5~‐deuteration in deuteriotrifluoroacetic acid.

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