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Synthesis and NMR Spectra of Substituted 1,4,5,8-Tetraazaphenanthrenes(TAP)

✍ Scribed by D. Maetens; D. Vandendijk; R. Nasielski-Hinkens

Publisher
Wiley (John Wiley & Sons)
Year
2010
Weight
219 KB
Volume
88
Category
Article
ISSN
0037-9646

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✦ Synopsis

Abstract

The synthesis of ring A substituted TAP'S starts from 5,6‐diaminoquinoxaline (II), which is condensed with n‐butylglyoxylate to give a mixture of 2‐ and 3‐hydroxy‐TAP, which reacted with POCl~3~/PCl~5~ to afford the corresponding monochlorocompound. Similarly, the condensation of II and ethyl oxalate produces 2,3‐dihydroxy‐TAP; this gives 2,3‐dichloro‐TAP with the same chlorinating agents. Nucleophilic substitution of the chlorine atom(s) (sodium methoxide, piperidine, hydrazine) occurs with high yields. The monohydrazino‐TAP's were oxidized into the corresponding monodeuterated derivatives, which allow an unambiguous assignment of the ^1^H NMR spectrum of TAP itself.

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