The reaction of 2′,3′,5′-tri-o-acyl-6-azauridines with dimethylchloromethyleneammonium chloride a synthesis of 6-azacytidine

✍ Scribed by J. Žemlička; J. Smrt; F. Šorm

• Book ID: 104212548
• Publisher: Elsevier Science
• Year: 1962
• Tongue: French
• Weight: 127 KB
• Volume: 3
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)70889-6

✦ Synopsis

DIMETHYLCHLOROMETHYLENEAMMONIUM chloride (II), readily available by reaction of phosgene or thionyl chloride with dimethylformamide, 192 is a highly reactive compound which has proved a versatile reagent in many fields of organic synthesis.3-8 The recently developed method for the preparation of acid chlorides by treatment of carboxylic acids or their salts with inorganic acid halides in the presence of catalytic amounts of dimethylformamide gives an interesting illustration of the action of (II) as a chlorinating reagent. This property of dimethylchloromethyleneammonium chloride (II) has also been exploited in the preparation of chlorinated derivatives of 1,3,5-triazine and of quinazoline. 8

We have now found that compound (II) will also react with a number of ' 2. Arnold, Coil. Czech. Chem. Comm. 2, 4048 (1959).