Iminophosphorane-mediated efficient synthesis of new tricyclic 3,5-dihydro-1,2,3-triazolo[4,5-d]-1,2,4-triazolo[1,5-a]pyrimidin-9-ones

The carbodiimides 2, obtained from aza-Wittig reactions of iminophosphorane 1 with aromatic isocyanates, reacted with hydrazine to give selectively 6-amino-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-ones 5. Compounds 5 were further transformed to iminophosphoranes 6 by reaction with triphenylphosphine, hex...

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Published in:Organic & biomolecular chemistry 2006-01, Vol.4 (1), p.130-134
Main Authors: Zhao, Jun-Feng, Xie, Chang, Xu, Sheng-Zhen, Ding, Ming-Wu, Xiao, Wen-Jing
Format: Article
Language:English
Subjects:
Crystallography, X-Ray
Imines - chemistry
Molecular Structure
Phosphoranes - chemistry
Pyrimidinones - chemical synthesis
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creator Zhao, Jun-Feng
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Xiao, Wen-Jing
description The carbodiimides 2, obtained from aza-Wittig reactions of iminophosphorane 1 with aromatic isocyanates, reacted with hydrazine to give selectively 6-amino-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-ones 5. Compounds 5 were further transformed to iminophosphoranes 6 by reaction with triphenylphosphine, hexachloroethane and triethylamine. A tandem aza-Wittig reaction of iminophosphorane 6 with isocyanate or acyl chloride generated previously unreported 3,5-dihydro-1,2,3-triazolo[4,5-d]-1,2,4-triazolo[1,5-a]pyrimidin-9-ones 10 or 12 in satisfactory yield. X-ray structure analysis of 10 g verified the proposed structure and the reaction selectivity.
doi_str_mv 10.1039/b513715b
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source Royal Society of Chemistry: Jisc Collections: Journals Archive 1841-2007 (2019-2023)
subjects Crystallography, X-Ray
Imines - chemistry
Molecular Structure
Phosphoranes - chemistry
Pyrimidinones - chemical synthesis
title Iminophosphorane-mediated efficient synthesis of new tricyclic 3,5-dihydro-1,2,3-triazolo[4,5-d]-1,2,4-triazolo[1,5-a]pyrimidin-9-ones
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