915068-44-9

Upstream product

• 915068-38-1 N-(5,5-dimethyl-2-phenylamino-4H-imidazol-4-on-3-yl)iminotriphenylphosphorane 
• 75-15-0 carbon disulfide 
• 915068-35-8 N-(1-ethoxycarbonyl-1-methylethyl)-N'-phenylcarbodiimide 
• 915068-37-0 3-amino-5,5-dimethyl-2-phenylamino-4H-imidazol-4-one 

Relevant academic research and scientific papers

New facile synthesis of 3,5-dihydro-6H-imidazo[1,2-b]-1,2,4-triazol-6-ones by an iminophosphorane-mediated annulation

Iminophosphorane 1 reacted with an aromatic isocyanate to unexpectedly give a mixture of carbodiimides 2, 3 and 4 through both the normal and the abnormal aza-Wittig reactions. 3-Aminoimidazolone 10 was obtained from the reaction of hydrazine hydrate with carbodiimide 2. Reaction of 10 with triphenyphosphane, hexachloroethane and triethylamine produced iminophosphorane 11 in good yield. A tandem aza-Wittig reaction of iminophosphorane 11 with isocyanate or CS 2 generated 3,5-dihydro-6H-imidazo[1,2-b]-1,2,4-triazol-6-ones 13 or 15 in satisfactory yield. Carbodiimides 18, obtained from normal aza-Wittig reactions of vinyl iminophosphorane 17 with aromatic isocyanates, reacted with hydrazine to give 2-arylamino-3-amino-4H-imidazol-4-ones 20. One-pot reactions of 2-arylamino-3-amino-4H-imidazol-4-ones 20 with isocyanates (or acyl chlorides), triphenyphosphane, hexachloroethane and triethylamine produced 3,5-dihydro-6H-imidazo[1,2-b]-1,2,4-triazol-6-ones 22 (or 23) in good yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.