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Synthesis 1991; 1991(11): 1026-1028
DOI: 10.1055/s-1991-26639
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N-[[(Chlorosulfinyl)oxy]methylene]-N-methylmethanaminium Chloride as A Dehydrating Agent. A Direct and Efficient One-Pot Synthesis of Various Pyrimidinones, Azetidinones and Pyridones via Cycloaddition Reactions

Satyendra P. Singh* , Asha R. Mahajan, Dipak Prajapati, Jagir S. Sandhu
  • *Division of Drugs and Pharmaceutical Chemistry Regional Research Laboratory, Jorhat 785 006, India
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Publication Date:
29 April 2002 (online)

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N-[[(Chlorosulfinyl)oxy]methylene]-N-methylmethanaminium chloride (1) is found to be an efficient and mild dehydrating agent for the in situ generation of monophenyl- (4a) diphenyl- (4b) and monochloroketenes (4c) directly from the corresponding carboxylic acids 2. These ketenes undergo cycloaddition reactions with 1,3-diaza-1, 3-butadienes 5 to afford 4(3H)-pyrimidinones 6 and azetidones 7, and with 3-(aryliminomethyl)chromones 8 to give [1]benzopyrano[3,2-c]pyridine-3,10[2H]diones 9.