Chromeno[2,3-d]pyrimidine-triones Synthesis by a Three-Component Coupling Reaction

被引:26
作者
Ghahremanzadeh, Ramin [1 ,2 ]
Fereshtehnejad, Fatemeh [1 ]
Bazgir, Ayoob [1 ]
机构
[1] Shahid Beheshti Univ, Dept Chem, Tehran 1983963113, Iran
[2] ACECR, Avicenna Res Inst, Nanobiotechnol Res Ctr, Tehran 196151177, Iran
关键词
chromeno[2,3-d]pyrimidine; cyclohexane-1,3-dione; barbituric acid; aldehyde; ONE-POT SYNTHESIS; IMMUNODEFICIENCY-VIRUS TYPE-1; EFFICIENT SYNTHESIS; DERIVATIVES; MICROWAVE; AGENTS; CYCLIZATION;
D O I
10.1248/cpb.58.516
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A simple and one-pot synthesis of new chromeno[2,3-d]pyrimidine-triones by a three-component condensation reaction of barbituric acids, aldehydes and cyclohexane-1,3-diones in refluxing ethanol in the presence of p-toluenesulfonic acid (p-TSA) for 3-10 h is reported. Two cyclohexane-1,3-diones, four barbituric acids and six substituted aldehydes were chosen for the library validation. Prominent among the advantages of this new method are operational simplicity, good yields and easy work-up procedures employed.
引用
收藏
页码:516 / 520
页数:5
相关论文
共 55 条
[1]   A new, one-pot, three-component synthesis of 4H-pyrido[1,2-a]-pyrimidines, 4H-pyrimido[1,2-a]pyrimidines, and 4H-pyrazino[ 1,2-a] pyrimidines [J].
Adib, Mehdi ;
Sayahi, Mohammad Hosein ;
Ziyadi, Hakimeh ;
Bijanzadeh, Hamid Reza ;
Zhu, Long-Guan .
TETRAHEDRON, 2007, 63 (45) :11135-11140
[2]   HIGHLY SPECIFIC-INHIBITION OF HUMAN IMMUNODEFICIENCY VIRUS TYPE-1 BY A NOVEL 6-SUBSTITUTED ACYCLOURIDINE DERIVATIVE [J].
BABA, M ;
TANAKA, H ;
DECLERCQ, E ;
PAUWELS, R ;
BALZARINI, J ;
SCHOLS, D ;
NAKASHIMA, H ;
PERNO, CF ;
WALKER, RT ;
MIYASAKA, T .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1989, 165 (03) :1375-1381
[3]   An efficient synthesis of spiro[dibenzo[b,i]xanthene-13,3′-indoline]-pentaones and 5H-dibenzo[b,i]xanthene-tetraones [J].
Bazgir, Ayoob ;
Tisseh, Zeinab Noroozi ;
Mirzaei, Peiman .
TETRAHEDRON LETTERS, 2008, 49 (35) :5165-5168
[4]   One-pot synthesis and antibacterial activities of pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine-dione derivatives [J].
Bazgir, Ayoob ;
Khanaposhtani, Maryam Mohammadi ;
Soorki, Ali Abolhasani .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (21) :5800-5803
[5]   A novel three-component method for the synthesis of triazolo[1,2-a]indazole-triones [J].
Bazgir, Ayoob ;
Seyyedhamzeh, Mozhdeh ;
Yasaei, Zahra ;
Mirzaei, Peiman .
TETRAHEDRON LETTERS, 2007, 48 (50) :8790-8794
[6]   5-SUBSTITUTED PYRIMIDINE NUCLEOSIDES AND NUCLEOTIDES [J].
BRADSHAW, TK ;
HUTCHINSON, DW .
CHEMICAL SOCIETY REVIEWS, 1977, 6 (01) :43-62
[7]  
Brown J.D., 1984, COMPREHENSIVE HETERO, V3, P57
[8]   SIMPLE NEW METHOD FOR THE SYNTHESIS OF 5-DEAZA-10-OXAFLAVIN, A POTENTIAL ORGANIC OXIDANT [J].
CHEN, X ;
TANAKA, K ;
YONEDA, F .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (02) :307-311
[9]   Study on the cyclization of 6-arylethynylpyrimidine-5-carbaldehydes with tert-butylamine: microwave versus thermal preparation of pyrido[4,3-d]pyrimidines [J].
Cikotiene, Inga ;
Kairys, Visvaldas ;
Buksnaitiene, Rita ;
Morkunas, Marius ;
Rudys, Simonas ;
Brukstus, Algirdas ;
Fernandes, Miguel X. .
TETRAHEDRON, 2009, 65 (29-30) :5752-5759
[10]   A novel reaction of 6-amino-uracils and isatins [J].
Dabiri, Minoo ;
Azimi, Seyyedeh Cobra ;
Khavasi, Hamid Reza ;
Bazgir, Ayoob .
TETRAHEDRON, 2008, 64 (30-31) :7307-7311