Biginelli-like three component reaction: Synthesis of some new ethyl 6-ethoxycarbonylmethyl-4-aryl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate derivatives

被引:19
作者
Azizian, Javad [1 ]
Mohammadi, Ali A. [1 ]
Kohshari, M. [1 ]
Karimi, Ali R. [1 ]
Mohammadizadeh, Mohammad R. [1 ]
机构
[1] Shahid Beheshti Univ, Fac Sci, Dept Chem, Tehran, Iran
关键词
D O I
10.1002/jhet.5570440228
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the context of our high-throughput organic synthesis program, we have studied the reactivity of special beta-keto esters toward the Biginelli reaction. We have found that a diethyl-3-oxoglutarate reacts with one molecule of urea and one molecule of aldehyde under solvent-free conditions to give a new family of 3,4-dihydropyrimidin-2(1H)-ones in good yields.
引用
收藏
页码:455 / 458
页数:4
相关论文
共 43 条
[1]   DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .3. 3-CARBAMOYL-4-ARYL-1,2,3,4-TETRAHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS ORALLY EFFECTIVE ANTIHYPERTENSIVE AGENTS [J].
ATWAL, KS ;
SWANSON, BN ;
UNGER, SE ;
FLOYD, DM ;
MORELAND, S ;
HEDBERG, A ;
OREILLY, BC .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :806-811
[2]   SUBSTITUTED 1,4-DIHYDROPYRIMIDINES .3. SYNTHESIS OF SELECTIVELY FUNCTIONALIZED 2-HETERO-1,4-DIHYDROPYRIMIDINES [J].
ATWAL, KS ;
ROVNYAK, GC ;
OREILLY, BC ;
SCHWARTZ, J .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5898-5907
[3]   A stereoselective three-component reaction:: One-pot synthesis of cis-isoquinolonic acids catalyzed by silica sulfuric acid under mild and heterogeneous conditions [J].
Azizian, J ;
Mohammadi, AA ;
Soleimani, E ;
Karimi, AR ;
Mohammadizadeh, MR .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (01) :187-190
[4]   A stereoselective three-component reaction:: KAl(SO4)2•12H2O, an efficient and reusable catalyst for the one-pot synthesis of cis-isoquinolonic acids [J].
Azizian, J ;
Mohammadi, AA ;
Karimi, AR ;
Mohammadizadeh, MR .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :350-352
[5]   A novel four-component reaction for the diastereoselective synthesis of some new spiro pyrrolizidines via 1,3-dipolar cycloaddition of azomethine ylides [J].
Azizian, J ;
Karimi, AR ;
Mohammadi, AA ;
Mohammadizadeh, MR .
SYNTHESIS-STUTTGART, 2004, (14) :2263-2265
[6]   An efficient one-pot procedure for preparation of 2,4(1H,3H)-qninazolinediones and 2-thioxoquinazolinone derivatives under microwave irradiation [J].
Azizian, J ;
Mohammadi, AA ;
Karimi, AR .
SYNTHETIC COMMUNICATIONS, 2003, 33 (03) :415-420
[7]   Synthesis of some novel γ-spiroiminolactones from reaction of cyclohexyl isocyanide and dialkyl acetylene dicarboxylates with 1-benzylisatin and tryptanthrine [J].
Azizian, J ;
Karimi, AR ;
Mohammadi, AA .
SYNTHETIC COMMUNICATIONS, 2003, 33 (03) :387-391
[8]   A novel one-pot, four component synthesis of some densely functionalized pyrroles [J].
Azizian, Javad ;
Karimi, Ali R. ;
Arefrad, Hamedeh ;
Mohammadi, Ali A. ;
Mohammadizadeh, M. R. .
MOLECULAR DIVERSITY, 2003, 6 (3-4) :223-226
[9]   A revision of the Biginelli reaction under solid acid catalysis. Solvent-free synthesis of dihydropyrimidines over montmorillonite KSF [J].
Bigi, F ;
Carloni, S ;
Frullanti, B ;
Maggi, R ;
Sartori, G .
TETRAHEDRON LETTERS, 1999, 40 (17) :3465-3468
[10]   A simplified green chemistry approach to the Biginelli reaction using 'Grindstone Chemistry' [J].
Bose, AK ;
Pednekar, S ;
Ganguly, SN ;
Chakraborty, G ;
Manhas, MS .
TETRAHEDRON LETTERS, 2004, 45 (45) :8351-8353