1,4-Diazabicyclo[2.2.2]octane-Catalyzed Multicomponent Domino Strategy for the Synthesis of Tetrasubstituted NH-Pyrroles

被引：10
作者：
Chang, Xiangqing
Yang, Xiaofeng
Chen, Zhiwei [1 ]
Zhong, Weihui [1 ]
机构：
[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China
来源：
SYNLETT | 2019年 / 30卷 / 12期
基金：
中国国家自然科学基金;
关键词：
multicomponent reaction; pyrroles; DABCO; cyclization; arylglyoxal monohydrates; enamino esters; ONE-POT SYNTHESIS; FLOW SYNTHESIS; KNORR; DERIVATIVES; ACCESS; FURANS;
D O I：
10.1055/s-0037-1611857
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A mild and efficient 1,4-diazabicyclo[2.2.2]octane (DABCO)-catalyzed three-component domino reaction was developed for the synthesis of highly functionalized NH-pyrroles from arylglyoxal monohydrates, enamino esters, and cyclic 1,3-dicarbonyl compounds in 1,4-dioxane at room temperature for 0.5 hours. Various substituted NH-pyrroles were obtained in moderate to good yields.
引用
收藏
页码：1431 / 1436
页数：6
相关论文
共 40 条
[1]   Versatility of Weinreb amides in the Knorr pyrrole synthesis [J].
Alberola, A ;
Ortega, AG ;
Sádaba, ML ;
Sañudo, C .
TETRAHEDRON, 1999, 55 (21) :6555-6566
[2]   Simple synthesis of substituted pyrroles [J].
Banik, BK ;
Samajdar, S ;
Banik, I .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (01) :213-216
[3]   A practical synthesis of a potent δ-opioid antagonist:: Use of a modified Knorr pyrrole synthesis [J].
Bellingham, RK ;
Carey, JS ;
Hussain, N ;
Morgan, DO ;
Oxley, P ;
Powling, LC .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2004, 8 (02) :279-282
[4]   Pyrrole: a resourceful small molecule in key medicinal hetero-aromatics [J].
Bhardwaj, Varun ;
Gumber, Divya ;
Abbot, Vikrant ;
Dhiman, Saurabh ;
Sharma, Poonam .
RSC ADVANCES, 2015, 5 (20) :15233-15266
[5]   Three-Component Povarov Reaction-Heteroannulation with Arynes: Synthesis of 5,6-Dihydroindolo[1,2-a]quinolines [J].
Bunescu, Ala ;
Wang, Qian ;
Zhu, Jieping .
ORGANIC LETTERS, 2014, 16 (06) :1756-1759
[6]   FeCl3 or MeSO3H-promoted multicomponent reactions for facile synthesis of structurally diverse furan analogues [J].
Chang, Xiangqing ;
Zhang, Xiongfei ;
Chen, Zhiwei .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (23) :4279-4287
[7]   An approach to the Paal-Knorr pyrroles synthesis catalyzed by Sc(OTf)3 under solvent-free conditions [J].
Chen, Jiuxi ;
Wu, Huayue ;
Zheng, Zhiguo ;
Jin, Can ;
Zhang, Xingxian ;
Su, Weike .
TETRAHEDRON LETTERS, 2006, 47 (30) :5383-5387
[8]   A Novel Method for One-pot Synthesis of Furo[3,2-c]coumarin Derivatives from 4-Hydroxycoumarin and Arylglyoxal under Microwave Irradiation [J].
Chen Zhiwei ;
Bi Jianhao ;
Su Weike .
CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (08) :1845-1850
[9]   Flow synthesis using gaseous ammonia in a Teflon AF-2400 tube-in-tube reactor: Paal-Knorr pyrrole formation and gas concentration measurement by inline flow titration [J].
Cranwell, Philippa B. ;
O'Brien, Matthew ;
Browne, Duncan L. ;
Koos, Peter ;
Polyzos, Anastasios ;
Pena-Lopez, Miguel ;
Ley, Steven V. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (30) :5774-5779
[10]   Polypyrrole thin films gas sensors [J].
de Souza, JEG ;
dos Santos, FL ;
Barros-Neto, B ;
dos Santos, CG ;
de Melo, CP .
SYNTHETIC METALS, 2001, 119 (1-3) :383-384
1234