Solvent-Free Heterocyclic Synthesis

被引:617
作者
Martins, Marcos A. P. [1 ]
Frizzo, Clarissa P. [1 ]
Moreira, Dayse N. [1 ]
Buriol, Lilian [1 ]
Machado, Pablo [1 ]
机构
[1] Univ Fed Santa Maria, Dept Quim, NUQUIMHE, BR-97105900 Santa Maria, RS, Brazil
关键词
ONE-POT SYNTHESIS; MICROWAVE-ASSISTED SYNTHESIS; SOLID-PHASE SYNTHESIS; MANNICH-TYPE REACTIONS; ONE-STEP SYNTHESIS; CONVERTING ENZYME-INHIBITORS; CATALYZED BIGINELLI REACTION; BACTERIAL PROTEIN-SYNTHESIS; POTENTIAL ANTITUMOR AGENTS; GRAM-POSITIVE BACTERIA;
D O I
10.1021/cr9001098
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The study of solvent-free heterocyclic synthesis reported that the solvent-free conditions are better than molecular solvents for cyclocondensation reactions; and the chemical mechanistic aspects of solvent-free reactions discussed are associated with cyclocondensation reactions. The use of solvent-free conditions in heterocyclic synthesis generally leads to similar or higher yields and a reduction in the reaction time as compared to the same reaction performed in the presence of molecular solvents. The experiments resulted that all reactions performed in MW, both domestic oven and synthesis equipment, presented better yields and shorter reaction times than those not carried out in MW. The E-factor for solvent-free reactions presented showed values in a range of 0.1-4.9 for reactions performed under solvent-free conditions considering only the synthetic steps and a range of 5.0-49.9 and 50.0-100.0 for reactions accomplished using molecular solvents.
引用
收藏
页码:4140 / 4182
页数:43
相关论文
共 696 条
[1]   KINETIC-STUDY ON THE ANNELATION OF HETEROCYCLES .1. QUINOXALINONE DERIVATIVES SYNTHESIZED BY HINSBERG REACTION [J].
ABASOLO, MI ;
GAOZZA, CH ;
FERNANDEZ, BM .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (06) :1771-1775
[2]   Intramolecular ring cleavage of chiral terpenoid-derived oxazinone via asymmetric anti-aldol reaction: Unexpected entry to a N-substituted tetrahydro-1,3-oxazine-2,4-dione derivative [J].
Abbas, TR ;
Cadogan, JIG ;
Doyle, AA ;
Gosney, I ;
Hodgson, PKG ;
Howells, GE ;
Hulme, AN ;
Parsons, S ;
Sadler, IH .
TETRAHEDRON LETTERS, 1997, 38 (27) :4917-4920
[3]   Novel and versatile methodology for synthesis of cyclic imides and evaluation of their cytotoxic, DNA binding, apoptotic inducing activities and molecular modeling study [J].
Abdel-Aziz, Alaa A. -M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2007, 42 (05) :614-626
[4]   An efficient synthesis of 3-amino-2-arylimidazo[1,2-a]pyridines [J].
Adib, Mehdi ;
Sheibani, Esmail ;
Zhu, Long-Guan ;
Mirzaei, Peiman .
TETRAHEDRON LETTERS, 2008, 49 (34) :5108-5110
[5]   The use of N-boc-1,3-oxazolidines as chiral auxiliaries in asymmetric synthesis [J].
Agami, C ;
Couty, F .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (04) :677-685
[6]   STEREOCHEMISTRY .60. KINETIC CONTROL OF ASYMMETRIC INDUCTION DURING OXAZOLIDINE FORMATION FROM (-)-EPHEDRINE AND AROMATIC-ALDEHYDES [J].
AGAMI, C ;
RIZK, T .
TETRAHEDRON, 1985, 41 (03) :537-540
[7]  
AGAMI C, 1999, TETRAHEDRON LETT, V40, P1977
[8]   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
[9]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[10]  
Ager DJ, 1997, ALDRICHIM ACTA, V30, P3