Chemical fixation of CO2: efficient synthesis of quinazoline-2,4(1H, 3H)-diones catalyzed by guanidines under solvent-free conditions

被引：89
作者：
Gao, Jian
He, Liang-Nian [1 ]
Miao, Cheng-Xia
Chanfreau, Sebastien
机构：
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
来源：
TETRAHEDRON | 2010年 / 66卷 / 23期
基金：
中国国家自然科学基金;
关键词：
Quinazolinedione; Aminobenzonitrile; Guanidine; Carbon dioxide; Solvent-free process; SUPERCRITICAL CARBON-DIOXIDE; SOLID-PHASE SYNTHESIS; CYCLIC CARBONATES; HIGHLY EFFICIENT; GREEN CHEMISTRY; PROPYLENE-OXIDE; DERIVATIVES; EPOXIDES; 1H-QUINAZOLINE-2,4-DIONES; 2,4(1H,3H)-QUINAZOLINEDIONES;
D O I：
10.1016/j.tet.2010.04.011
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Guanidines were proved to be efficient catalysts for the chemical fixation of carbon dioxide with 2-aminobenzonitriles under solvent-free conditions. Notably, the catalysts with low loading worked well for a variety of 2-aminobenzonitriles. As a result, quinazoline-2,4(1H, 3H)-diones by employing present protocol were obtained in good yields under mild conditions. This process represents an alternative approach for the greener chemical fixation of CO2 to afford valuable compounds. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4063 / 4067
页数：5
相关论文
共 57 条
[1]   Life cycle assessment and green chemistry: the yin and yang of industrial ecology [J].
Anastas, PT ;
Lankey, RL .
GREEN CHEMISTRY, 2000, 2 (06) :289-295
[2]   Meeting the challenges to sustainability through green chemistry [J].
Anastas, PT .
GREEN CHEMISTRY, 2003, 5 (02) :G29-G34
[3]   The chemistry and biology of organic guanidine derivatives [J].
Berlinck, Roberto G. S. ;
Burtoloso, Antonio Carlos B. ;
Kossuga, Miriam H. .
NATURAL PRODUCT REPORTS, 2008, 25 (05) :919-954
[4]   Electrophilic N-amination of two quinazoline-2,4-diones using substituted (nitrophenyl)hydroxylamines [J].
Boyles, DC ;
Curran, TT ;
Parlett, RV .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2002, 6 (03) :230-233
[5]   Substituted isoquinolines and quinazolines as potential antiinflammatory agents.: Synthesis and biological evaluation of inhibitors of tumor necrosis factor α [J].
Chao, Q ;
Deng, L ;
Shih, HC ;
Leoni, LM ;
Genini, D ;
Carson, DA ;
Cottam, HB .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (19) :3860-3873
[6]  
Choo HYP, 2002, BIOORGAN MED CHEM, V10, P517
[7]   Green Chemistry: challenges and opportunities [J].
Clark, JH .
GREEN CHEMISTRY, 1999, 1 (01) :1-8
[8]   Superbase catalysis of oxazolidin-2-one ring formation from carbon dioxide and prop-2-yn-1-amines under homogeneous or heterogenous conditions [J].
Costa, M ;
Chiusoli, GP ;
Taffurelli, D ;
Dalmonego, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (09) :1541-1546
[9]   Guanidinium salt functionaiized PEG:: An effective and recyclable homogeneous catalyst for the synthesis of cyclic carbonates from CO2 and epoxides under solvent-free conditions [J].
Dou, Xiao-Yong ;
Wang, Jin-Quan ;
Du, Ya ;
Wang, Er ;
He, Liang-Nian .
SYNLETT, 2007, (19) :3058-3062
[10]   A poly(ethylene glycol)-supported quaternary ammonium salt for highly efficient and environmentally friendly chemical fixation Of CO2 with epoxides under supercritical conditions [J].
Du, Y ;
Wang, JQ ;
Chen, JY ;
Cai, F ;
Tian, JS ;
Kong, DL ;
He, LN .
TETRAHEDRON LETTERS, 2006, 47 (08) :1271-1275
123456