1-Aryl-3-(carbamoylmethyl)triazenes:  Synthesis, Spectroscopic Analysis and Cyclization to New 1,2,3-Benzotriazines

Reaction of a series of arene diazonium salts with glycinamide affords the N-coupling products the 1-aryl-3-(carbamoylmethyl)triazenes, ArN=NNHCH2CONH2 3, which have been characterized by 1H and 13C NMR spectroscopy. The reaction works well with electron withdrawing groups in the ortho- or para-posi...

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Bibliographic Details
Published in:Journal of organic chemistry 1996-01, Vol.61 (1), p.210-214
Main Authors: Jollimore, Jason V, Vaughan, Keith, Hooper, Donald L
Format: Article
Language:English
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Summary:Reaction of a series of arene diazonium salts with glycinamide affords the N-coupling products the 1-aryl-3-(carbamoylmethyl)triazenes, ArN=NNHCH2CONH2 3, which have been characterized by 1H and 13C NMR spectroscopy. The reaction works well with electron withdrawing groups in the ortho- or para-position of the aryl moiety, but when the coupling reaction was attempted with a p-bromo-substituted diazonium salt, the reaction afforded the pentazadiene 8 and not the expected triazene. Triazenes with a reactive ester or cyano-substituent in the ortho-position of the benzene ring were found to undergo spontaneous cyclization to the respective 1,2,3-benzotriazine heterocycles 4a and 5. The 3-(carbamoylmethyl)-4-imino-1,2,3-benzotriazine (5) was characterized by further NMR experiments, 15N NMR, and homonuclear correlated NMR spectra.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo951279i