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Complete 1H, 13C and 15N NMR assignment of tirapazamine and related 1,2,4-benzotriazine N-oxides

✍ Scribed by Maruta Boyd; Michael P. Hay; Peter D. W. Boyd

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
183 KB
Volume
44
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

^1^H, ^13^C and ^15^N NMR measurements (1D and 2D including ^1^H^15^N gs‐HMBC) have been carried out on 3‐amino‐1, 2,4‐benzotriazine and a series of N‐oxides and complete assignments established. N‐Oxidation at any position resulted in large upfield shifts of the corresponding N‐1 and N‐2 resonances and downfield shifts for N‐4 with the exception of the 3‐amino‐1,2,4‐benzotriazine 1‐oxide in which a small upfield shift of N‐4 was observed. Density functional GIAO calculations of the ^15^N and ^13^C chemical shifts [B3LYP/6‐31G(d)//B3LYP/6‐311 + G(2d,p)] gave good agreement with experimental values confirming the assignments. The combination of ^13^C and ^15^N NMR provides an unambiguous method for assigning the ^1^H and ^13^C resonances of N‐oxides of 1,2,4‐benzotriazines. Copyright © 2006 John Wiley & Sons, Ltd.

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