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
[41]   HYDROXY SCHIFF BASE-OXAZOLIDINE TAUTOMERISM - APPARENT BREAKDOWN OF BALDWIN RULES [J].
ASTUDILLO, MEA ;
CHOKOTHO, NCJ ;
JARVIS, TC ;
JOHNSON, CD ;
LEWIS, CC ;
MCDONNELL, PD .
TETRAHEDRON, 1985, 41 (24) :5919-5928
[42]   Solvent-free reaction of some 1,2-diaza-1,3-butadienes with phosphites:: Environmentally friendly access to new diazaphospholes and E-hydrazonophosphonates [J].
Attanasi, OA ;
Baccolini, G ;
Boga, C ;
De Crescentini, L ;
Filippone, P ;
Mantellini, F .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4033-4037
[43]   POTENTIAL ANTITUMOR AGENTS .50. INVIVO SOLID-TUMOR ACTIVITY OF DERIVATIVES OF N-[2-(DIMETHYLAMINO)ETHYL]ACRIDINE-4-CARBOXAMIDE [J].
ATWELL, GJ ;
REWCASTLE, GW ;
BAGULEY, BC ;
DENNY, WA .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (04) :664-669
[44]   FROM ALLENIC PHOSPHORUS DERIVATIVES TO HETEROCYCLIC-COMPOUNDS - SYNTHESIS OF A 1,2,3-DIAZAPHOSPHOLE COMPOUND WITH A STRONGLY POLAR NH GROUP LINKED TO A DICOORDINATE PHOSPHORUS ATOM [J].
AYED, N ;
BACCAR, B ;
MATHIS, F ;
MATHIS, R .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1985, 21 (03) :335-347
[45]  
Azas Nadine, 2003, Farmaco (Lausanne), V58, P1263, DOI 10.1016/j.farmac.2003.07.009
[46]   BENZOTHIADIPHOSPHOLE AS PHOSPHORUS DONATING REAGENT FOR A NEW ROUTE TO 2H-1,2,3-DIAZAPHOSPHOLE DERIVATIVES [J].
BACCOLINI, G ;
ORSOLAN, G ;
MEZZINA, E .
TETRAHEDRON LETTERS, 1995, 36 (03) :447-450
[47]   Solid-phase synthesis of difficult peptide sequences at elevated temperatures:: A critical comparison of microwave and conventional heating technologies [J].
Bacsa, Bernadett ;
Horvati, Kata ;
Bosze, Szilvia ;
Andreae, Fritz ;
Kappe, C. Oliver .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) :7532-7542
[48]   Highly efficient synthesis of pyrimidines under microwave-assisted conditions [J].
Bagley, MC ;
Hughes, DD ;
Taylor, PH .
SYNLETT, 2003, (02) :259-261
[49]   Synthesis of functionalised oxazoles and bis-oxazoles [J].
Bagley, MC ;
Buck, RT ;
Hind, SL ;
Moody, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (03) :591-600
[50]   Aromaticity as a cornerstone of heterocyclic chemistry [J].
Balaban, AT ;
Oniciu, DC ;
Katritzky, AR .
CHEMICAL REVIEWS, 2004, 104 (05) :2777-2812