One-pot synthesis of tetrazolo[1,5-a]pyrimidines under solvent-free conditions

被引:28
作者
Ghorbani-Vaghei, Ramin [1 ]
Toghraei-Semiromi, Zahra [1 ]
Amiri, Mostafa [1 ]
Karimi-Nami, Rahman [2 ]
机构
[1] Bu Ali Sina Univ, Dept Organ Chem, Fac Chem, Hamadan 65174, Iran
[2] Univ Tehran, Univ Coll Sci, Sch Chem, Tehran, Iran
关键词
Tetrazolo[1,5-a]pyrimidines; Multicomponent reaction; Aldehyde; Ketone; Solvent-free; TBBDA; PYRIMIDINE; ACID;
D O I
10.1007/s11030-013-9435-0
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of 5,7-diaryl-4,7-dihydrotetrazolo[1,5-a]pyrimidines and 5-methyl-7-aryl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylates were obtained from aryl aldehydes, 2-aminotetrazole, substituted acetophenones, or ethyl acetoacetate in good to excellent yields by proceeding through a simple, mild, and efficient procedure utilizing ,,,-tetrabromobenzene-1,3-disulfonamide as catalyst.
引用
收藏
页码:307 / 318
页数:12
相关论文
共 28 条
[1]   Synthesis of 2,4,6-trisubstituted pyrimidines as antimalarial agents [J].
Agarwal, A ;
Srivastava, K ;
Puri, SK ;
Chauhan, PMS .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (15) :4645-4650
[2]  
Azas Nadine, 2003, Farmaco (Lausanne), V58, P1263, DOI 10.1016/j.farmac.2003.07.009
[3]  
Brown D.J., 1994, PYRIMIDINES, V52
[4]  
Desenko S.M., 2001, Chem. Heterocycl. Comp, V37, P747, DOI [10.1023/A:1011925631511, DOI 10.1023/A:1011925631511]
[5]   A substituted tetrahydro-tetrazolo-pyrimidine is a specific and novel inhibitor of hepatitis B virus surface antigen secretion [J].
Dougherty, Anne Marie ;
Guo, Haitao ;
Westby, Gael ;
Liu, Yuanjie ;
Simsek, Ender ;
Guo, Ju-Tao ;
Mehta, Anand ;
Norton, Pamela ;
Gu, Baohua ;
Block, Timothy ;
Cuconati, Andrea .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2007, 51 (12) :4427-4437
[6]   Synthesis of 6-acyl-7-aryl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-5-carboxylic acids and their methyl esters [J].
Gein, V. L. ;
Gein, L. F. ;
Tsyplyakova, E. P. ;
Panova, O. S. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 43 (09) :1382-1386
[7]   Synthesis of alkyl 5-aryl-7-methyl-1,5-dihydrotetrazolo-[1,5-a]pyrimidine-6-carboxylates [J].
Gein, V. L. ;
Vladimirov, I. N. ;
Fedorova, O. V. ;
Kurbatova, A. A. ;
Nosova, N. V. ;
Krylova, I. V. ;
Vakhrin, M. I. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (05) :699-705
[8]   Ionic liquid promoted novel and efficient one pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones at ambient temperature under ultrasound irradiation [J].
Gholap, AR ;
Venkatesan, K ;
Daniel, T ;
Lahoti, RJ ;
Srinivasan, KV .
GREEN CHEMISTRY, 2004, 6 (03) :147-150
[9]   Mild and regioselective bromination of aromatic compounds with N,N,N′,N′-tetrabromobenzene-1,3-disulfonylamide an poly (N-bromobenzene-1,3-di-sulfonylamide) [J].
Ghorbani-Vaghei, R ;
Jalili, H .
SYNTHESIS-STUTTGART, 2005, (07) :1099-1102
[10]   Poly(N-bromobenzene-1,3-disulfonamide) and N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide as novel catalytic reagents for silylation of alcohols, phenols, and thiols using hexamethyldisilazane [J].
Ghorbani-Vaghei, Ramin ;
Zolfigol, Mohammad Ali ;
Chegeny, Mahdieh ;
Veisi, Hojat .
TETRAHEDRON LETTERS, 2006, 47 (26) :4505-4508