Fast and Green One-Pot Multicomponent Synthesis of a Library of Pyrrolo[1,2-c]Pyrimidines Under Microwave Irradiation

被引:11
作者
Georgescu, Emilian [1 ]
Georgescu, Florentina [1 ]
Draghici, Constantin [2 ]
Cristian, Liliana [2 ]
Popa, Marcel Mirel [2 ]
Dumitrascu, Florea [2 ]
机构
[1] Res Ctr Oltchim, Ramnicu Valcea 240050, Romania
[2] Romanian Acad, Ctr Organ Chem CD Nenitzescu, Bucharest 060023, Romania
关键词
1,3-dipolar cycloaddition; microwaves; multicomponent reaction; N-ylide; pyrrolo[1,2-c]pyrimidine; PYRIMIDINIUM YLIDES; 4-METHYLPYRIMIDINIUM YLIDES; 1,3-DIPOLAR CYCLOADDITION; 3-COMPONENT SYNTHESIS; ASSISTED SYNTHESIS; HETEROCYCLES; REACTIVITY; STABILITY; EFFICIENT; DERIVATIVES;
D O I
10.2174/13862073113169990050
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
A simple, clean and rapid one-pot three component, microwave-assisted synthesis of pyrrolo[1,2-c]pyrimidine derivatives starting from various substituted pyrimidines, 2-bromoacetophenones and nonsymmetrical, electron deficient alkynes in 1,2-epoxybutane which acts both as solvent and acid scavenger is reported. This one-pot three component synthesis implies short reaction times being at the same time highly cost-effective and environmental friendly. [GRAPHICS] .
引用
收藏
页码:851 / 857
页数:7
相关论文
共 48 条
[1]   Synthesis of 1,2-dihydropyrrolo[1,2-c]pyrimidin-1-ones [J].
Alvarez, M ;
Fernández, D ;
Joule, JA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (03) :249-255
[2]   Application of Selective Palladium-Mediated Functionalization of the Pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine Heterocyclic System for the Total Synthesis of Variolin B and Deoxyvariolin B [J].
Baeza, Alejandro ;
Mendiola, Javier ;
Burgos, Carolina ;
Alvarez-Builla, Julio ;
Vaquero, Juan J. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (29) :5607-5618
[3]   Microwave-assisted synthesis of bioactive quinazolines and quinazolinones [J].
Besson, Thierry ;
Chosson, Elizabeth .
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2007, 10 (10) :903-917
[4]   Additional bioactive guanidine alkaloids from the Mediterranean sponge Crambe crambe [J].
Bondu, Stephanie ;
Genta-Jouve, Gregory ;
Leiros, Marta ;
Vale, Carmen ;
Guigonis, Jean-Marie ;
Botana, Luis M. ;
Thomas, Olivier P. .
RSC ADVANCES, 2012, 2 (07) :2828-2835
[5]   SAUREAMID-REAKTIONEN, .22. SYNTHESE VON PYRIMIDINEN MITTELS TRIS-FORMAMINO-METHANS [J].
BREDERECK, H ;
GOMPPER, R ;
GEIGER, B .
CHEMISCHE BERICHTE-RECUEIL, 1960, 93 (06) :1402-1406
[6]   Contributions to syntheses of pyrrolo[2,1-a]phthalazines [J].
Caira, Mino R. ;
Georgescu, Emilian ;
Georgescu, Florentina ;
Albota, Florin ;
Dumitrascu, Florea .
MONATSHEFTE FUR CHEMIE, 2011, 142 (07) :743-748
[7]   A NEW APPROACH FOR THE SYNTHESIS OF FUSED PYRROLES - THE SYNTHESIS OF ACYL SUBSTITUTED PYRROLO[1,2-X]AZINES [J].
COPAR, A ;
STANOVNIK, B ;
TISLER, M .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (06) :1577-1579
[8]   A concise diastereoselective approach to the left-hand side of batzelladine A [J].
Davies, Christopher D. ;
Elliott, Mark C. ;
Hill-Cousins, Joseph ;
Khan, Misbah-ul A. ;
Maqbool, Tahir ;
Wood, John L. .
SYNLETT, 2008, (13) :2028-2032
[9]  
de la Hoz A, 2007, COMB CHEM HIGH T SCR, V10, P877
[10]   PYRIMIDINIUM N-DICYANOMETHYLIDE - SYNTHESIS AND REACTIVITY TOWARDS DIMETHYL ACETYLENEDICARBOXYLATE [J].
DELAHOZ, A ;
DEPAZ, JLG ;
DIEZBARRA, E ;
ELGUERO, J ;
PARDO, C .
HETEROCYCLES, 1986, 24 (12) :3473-3476