1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU): as a highly efficient bicyclic amidine catalyst promoted solvent-free and one-pot synthesis of 1H-pyrazolo [1, 2-b] phthalazine-5,10-dione derivatives

被引:0
作者
Mohamadpour, Farzaneh [1 ]
机构
[1] Apadana Inst Higher Educ, Sch Engn, Shiraz, Iran
来源
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY | 2020年 / 59卷 / 08期
关键词
1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU); Highly efficient bicyclic amidine catalyst; 1H-pyrazolo; 1; 2-b; phthalazine-5; 10-dione derivatives; Solvent-free conditions; One-pot procedure; GREEN SYNTHESIS; BIODEGRADABLE CATALYST; 4-COMPONENT SYNTHESIS; 3-COMPONENT REACTION; ACID; CAFFEINE; FACILE;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) as a highly efficient bicyclic amidine catalyst promoted one-pot multi-component synthesis of biologically active 1H-pyrazolo [1, 2-b] phthalazine-5, 10-dione derivatives via one-pot four-component condensation reaction of phthalimide, hydrazine monohydrate, aryl aldehydes and malononitrile under solvent-free conditions through simple filter with no necessity of chromatographic purification steps. Use of safe, non-volatile, non-corrosive, highly efficient, readily available and easy to handle of catalyst, one-pot reaction, high yields and short reaction times, economical and convenient synthesis, solvent-free conditions and operational simplicity are among the other added advantages that make this approach an attractive alternative for the synthesis of these biologically active compounds.
引用
收藏
页码:1234 / 1242
页数:9
相关论文
共 40 条
[1]   Superior amine catalysts for the Baylis-Hillman reaction: the use of DBU and its implications [J].
Aggarwal, VK ;
Mereu, A .
CHEMICAL COMMUNICATIONS, 1999, (22) :2311-2312
[2]   Nucleophilicities and carbon basicities of DBU and DBN [J].
Baidya, M. ;
Mayr, Herbert .
CHEMICAL COMMUNICATIONS, 2008, (15) :1792-1794
[3]   Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: Lead identification and SAR of 3-and 4-substituted derivatives [J].
Genin, MJ ;
Biles, C ;
Keiser, BJ ;
Poppe, SM ;
Swaney, SM ;
Tarpley, WG ;
Yagi, Y ;
Romero, DL .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (05) :1034-1040
[4]   An efficient one-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives [J].
Ghahremanzadeh, Ramin ;
Shakibaei, Ghazaleh Imani ;
Bazgir, Ayoob .
SYNLETT, 2008, (08) :1129-1132
[5]   One-pot synthesis of 1H-pyrazolo[1,2-b] phthalazine-5,10-dione derivatives under solvent-free conditions [J].
Ghorbani-Vaghei, Ramin ;
Noori, Samira ;
Toghraei-Semiromi, Zahra ;
Salimi, Zahra .
RSC ADVANCES, 2014, 4 (89) :47925-47928
[6]   Synthesis and anticonvulsant activity of novel and potent 6,7-methylenedioxyphthalazin-1(2H)-ones [J].
Grasso, S ;
De Sarro, G ;
De Sarro, A ;
Micale, N ;
Zappalà, M ;
Puja, G ;
Baraldi, M ;
De Micheli, C .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (15) :2851-2859
[7]  
Im YJ, 2001, B KOR CHEM SOC, V22, P1053
[8]  
Kakkerla R, 2018, INDIAN J CHEM B, V57, P823
[9]   DBU: a highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3-b]pyranes, 2-amino-4H-benzo[h]chromenes and 2-amino-4H benzo[g]chromenes in aqueous medium [J].
Khurana, Jitender M. ;
Nand, Bhaskara ;
Saluja, Pooja .
TETRAHEDRON, 2010, 66 (30) :5637-5641
[10]   Synthesis of 1-/2-substituted-[1,2,3]triazolo[4,5-g]phthalazine4,9-diones and evaluation of their cytotoxicity and topoisomerase II inhibition [J].
Kim, Jin Sung ;
Rhee, Hee-Kyung ;
Park, Hyen Joo ;
Lee, Sang Kook ;
Lee, Chong-Ock ;
Choo, Hea-Young Park .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (08) :4545-4550