A novel microwave-assisted one-pot synthesis of pyrano[2,3-d]pyrimidines and pyrido[2,,3-d]pyrimidines via a three component reaction in solvent-free condition

被引:37
作者
Devi, I [1 ]
Bhuyan, PJ [1 ]
机构
[1] Reg Res Lab, Div Med Chem, Jorhat 785006, Assam, India
关键词
solvent-free reaction; multicomponent reaction; microwave-assisted reaction; pyrano[2,3-d]pyrimidines; pyrido[2,3-d]pyrimidines;
D O I
10.1055/s-2003-43367
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three-component cyclocondensation of barbituric acids 1, triethylorthoformate. 2 and alkyl nitriles 3 in presence of acetic anhydride proceeds under microwave-assisted conditions to give pyrano[2,3-d]pyrimidines 4 in excellent yields. 6-Aminouracils 5 or 6-hydroxy-aminouracils 7 react with 2 and 3 under identical conditions to yield pyrido[2,3-d]pyrimidines 6 or pyrido[2,3-d]pyrimidine oxides 8 in high yields.
引用
收藏
页码:283 / 286
页数:4
相关论文
共 49 条
[31]  
Huma HZS, 2002, TETRAHEDRON LETT, V43, P6485
[32]   Synthesis of pyrrolo[1,2-a]quinoxaline and its 4-(1-hydroxyalkyl) derivatives by Lewis acid-catalyzed reactions of 1-(2-isocyanophenyl)pyrrole [J].
Kobayashi, K ;
Matoba, T ;
Irisawa, S ;
Matsumoto, T ;
Morikawa, O ;
Konishi, H .
CHEMISTRY LETTERS, 1998, (06) :551-552
[33]  
KRETZSCHMAR E, 1980, PHARMAZIE, V35, P253
[34]  
List B, 2001, SYNLETT, P1687
[35]   A novel synthesis of 2-aminopyrroles using a three-component reaction [J].
Nair, V ;
Vinod, AU ;
Rajesh, C .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) :4427-4429
[36]   Highly enantioselective approach to indolizidines:: Preparation of (+)-(1S,8aS)-1-hydroxyindolizidine and (-)-slaframine [J].
Pourashraf, M ;
Delair, P ;
Rasmussen, MO ;
Greene, AE .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21) :6966-6972
[37]   A theory of the mechanism of the phyto-chemical synthesis of certain alkaloids. [J].
Robinson, R .
JOURNAL OF THE CHEMICAL SOCIETY, 1917, 111 :876-899
[38]   Stereoselective U-4CRs with 1-amino-5-desoxy-5-thio-2,3,4-O-isobutanoyl-β-D-xylopyranose -: an effective and selectively removable chiral auxiliary [J].
Ross, GF ;
Herdtweck, E ;
Ugi, I .
TETRAHEDRON, 2002, 58 (30) :6127-6133
[39]  
Sakuma Y., 1989, Chem. Abstr, V115, P71646, Patent No. [WO 91/05785, 9105785]
[40]   One-step synthesis of substituted 6-amino-5-cyanospiro-4-(piperidine-4′)-2H,4H-dihydropyrazolo[3,4-b]pyrans [J].
Shestopalov, AM ;
Emeliyanova, YM ;
Shestopalov, AA ;
Rodinovskaya, LA ;
Niazimbetova, ZI ;
Evans, DH .
ORGANIC LETTERS, 2002, 4 (03) :423-425