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Synthesis of sulfonamides and 1,3-oxazine-2,4-diones from arylsulfonyl isocyanates and diketene.

  作者 Alizadeh, Abdolali;Zohreh, Nasrin;Zhu, Long-Guan;  
  选自 期刊  Synthesis;  卷期  2008年-13;  页码  2073-2076  
  关联知识点  
 

[摘要]An effective route to functionalized N1-[(2,6-dimethyl-4-oxo-4H-pyran-3-yl)carbonyl]-1-arylsulfonamide and 3-(arylsulfonyl)-6-methyl-2H-1,3-oxazine-2,4(3H)-dione derivs. was described. This involves the reaction of arylsulfonyl isocyanates and diketene in the presence of N-heteroarom. compds. such as 1,3,5-triazine, 1-methyl-1H-imidazole, or pyridine as catalyst. The reactive 1:1 zwitterions obtained from the addn. of N-heteroarom. compd. to arylsulfonyl isocyanates were trapped by diketene to produce functionalized sulfonamide and 1,3-oxazine-2,4(3H)-dione derivs. The structure of N1-[(2,6-dimethyl-4-oxo-4H-pyran-3-yl)carbonyl]-1-tolylsulfonamide was confirmed by single crystal x-ray diffraction anal. [triclinic, P-1, a 7.3885(9), b 8.1143(10), c 14.1248(18) ? a 76.866(1), b 79.723(1), g 69.187(1)? V 766.40(16) ?, Z 2].

 
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