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One Pot Synthesis of Spiro Pyrimidinethiones/Spiro Pyrimidinones, Quinazolinethiones/Quinazolinones, and Pyrimidopyrimidines

  作者 GUPTA POONAM; GUPTA SHALLU; SACHAR ANAND; KOUR DALJEET; SINGH JASBIR; SHARMA RATTAN L  
  选自 期刊  Journal of Heterocyclic Chemistry;  卷期  2010年47-2;  页码  324-333  
  关联知识点  
 

[摘要]Condensation of cyclohexane-1,3-dione/barbituric acid, thiourea/urea, and aromatic aldehyde in the mole ratio of 1:1:3 in solventless reaction in presence of NiCl2/KI afforded 1,5-diaryl-3-thioxo-2,4-diazaspiro[5.5]-undecane-7,11-dione/1,5-diaryl- 2,4-diazaspiro[5.5] undecane-3,7,11-trione analogues and 7,1 1-diaryl-9-thioxo-2,4,8,10-tetraazaspiro[5.5]undecane-1,3,5,-trione/7, II -diaryl-2,4,8,10-tetraazaspiro[5.5]undecane-1,3,5,9-tetraone analogues, respectively. The similar condensation of cyclohexane-1,3-dione/cyclohexanone, thiourea/urea, and aromatic aldehyde/heteroaromatic aldehyde in the mole ratio of 1:1:1 in refluxing methanol afforded 4-aryl/heteroaryl-2-thioxo-1,2,3,4,5,6,7,8-octahydroquinazolin-5-one,4a ryl/heteroaryl-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-dione analogues and 4-aryl/heteroaryl-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thione, 4-aryl/heteroaryl-1,2,3,4,5,6,7,8-octahydroquinazol in-2-one analogues, respectively. Condensation of heterocyclic active methylene compound, barbituric acid, thiourea/urea, and aromatic aldehydes under similar set of conditions in 1:1:1 mole ratio was carried which afforded 5-aryl-7-thioxo- 1,2,3,4,5,6,7,8-octahydropyrimido[4,5-d]pyrimidine-2,4-dione/5-aryl- 1,2,3,4,5, 6,7,8-octahydropyrimido[4,5-d]pyrimidine-2,4,7-trione analogues. Similar condensation of an active methine compound, 2-acetylcyclohexanone, thiourea/urea, and aromatic aldehydes in the mole ratio of 1:1:1 produced 5-aryl-1-methyl-3-thioxo-2,4-diazaspiro[5.5]undec-1-en-7-one/5-aryl-1-m ethyl-2, 4-diazaspiro[5.5]undec-1-ene-3,7-dione analogues, the spiro compounds of entirely different kind. All these identifications and characterizations have been based on the elemental analysis and spectral data.

 
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