One-Pot AgOAc-Mediated Synthesis of Polysubstituted Pyrroles from Primary Amines and Aldehydes: Application to the Total Synthesis of Purpurone

被引:105
作者
Li, Qingjiang [1 ]
Fan, Aili [1 ]
Lu, Zhiyao [1 ]
Cui, Yuxin [1 ]
Lin, Wenhan [1 ]
Jia, Yanxing [1 ,2 ]
机构
[1] Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
[2] Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
基金
中国国家自然科学基金;
关键词
EFFICIENT TOTAL-SYNTHESIS; C BOND FORMATION; LEAD-TETRAACETATE; ENAMINE-ESTERS; SUBSTITUTED PYRROLES; SEQUENTIAL REACTIONS; DIRECT ANNULATION; ALPHA-ARYLATION; OXIDATION; ALKALOIDS;
D O I
10.1021/ol101644g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient method for the synthesis of 1,3,4-trisubstituted or 3,4-disubstituted pyrroles has been developed. The reaction represents the first time that pyrroles are synthesized directly from readily available aldehydes and amines (anilines) as starting materials. This method has been successfully applied to the rapid synthesis of purpurone.
引用
收藏
页码:4066 / 4069
页数:4
相关论文
共 50 条
[21]   Efficient one-pot room-temperature synthesis of 2-imidazolines from aldehydes [J].
Alinezhad, H. ;
Nemati, K. ;
Zare, M. .
BULGARIAN CHEMICAL COMMUNICATIONS, 2015, 47 (03) :804-808
[22]   Convenient One-Pot Synthesis of N-Substituted 3-Trifluoroacetyl Pyrroles [J].
Zanatta, Nilo ;
Wouters, Aria D. ;
Fantinel, Leonardo ;
da Silva, Fabio M. ;
Barichello, Rosemario ;
da Silva, Pedro E. A. ;
Ramos, Daniela F. ;
Bonacorso, Helio G. ;
Martins, Marcos A. P. .
SYNLETT, 2009, (05) :755-758
[23]   One-Pot Metal-Free Cascade Synthesis of 2-(Perfluoroalkyl)pyrroles [J].
Sun, Xuechun ;
Han, Jing ;
Chen, Jie ;
Deng, Hongmei ;
Shao, Min ;
Zhang, Hui ;
Cao, Weiguo .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (32) :7086-7090
[24]   Synthesis of polysubstituted pyrroles via Ag(I)-mediated conjugate addition and cyclization reaction of terminal alkynes with amines [J].
Chong, Qinglei ;
Xin, Xiaoyi ;
Wang, Chunxiang ;
Wu, Fan ;
Wan, Boshun .
TETRAHEDRON, 2014, 70 (02) :490-494
[25]   Copper-Promoted Regioselective Synthesis of Polysubstituted Pyrroles from Aldehydes, Amines, and Nitroalkenes via 1,2-Phenyl/Alkyl Migration [J].
Andreou, Dimitrios ;
Kallitsakis, Michael G. ;
Loukopoulos, Edward ;
Gabriel, Catherine ;
Kostakis, George E. ;
Lykakis, Ioannis N. .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (04) :2104-2113
[26]   Polyethylene glycol (PEG-400) as an efficient and recyclable reaction medium for one-pot synthesis of polysubstituted pyrroles under catalyst-free conditions [J].
Nagarapu, Lingaiah ;
Mallepalli, Raghu ;
Yeramanchi, Lingappa ;
Bantu, Rajashaker .
TETRAHEDRON LETTERS, 2011, 52 (26) :3401-3404
[27]   A one-pot chemoselective synthesis of secondary amines by using a biomimetic electrocatalytic system [J].
Largeron, Martine .
ELECTROCHIMICA ACTA, 2009, 54 (22) :5109-5115
[28]   A Facile One-Pot Synthesis of Chloropyridines from Chalcones [J].
Menon, Prasanth K. ;
Krishnaraj, K. U. ;
George, Sholly C. ;
Devaky, K. S. ;
Anabha, E. R. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (05) :1385-1389
[29]   Simple and Efficient One-Pot Synthesis of 2-Substituted Benzimidazoles from -Diaminoarene and Aryl Aldehydes [J].
Alapati, Mohan Lakshmi Punna Rao ;
Abburi, Sridhar Rao ;
Mukkamala, Saratchandra Babu ;
Rao, M. Krishnaji .
SYNTHETIC COMMUNICATIONS, 2015, 45 (21) :2436-2443
[30]   Novel One-Pot Cyclization of the Blaise Reaction Intermediate and Arylglyoxals: The Synthesis of Substituted NH -Pyrroles [J].
Chen, Zhiwei ;
Chen, Hao ;
Yang, Xiaofeng ;
Chang, Xiangqing .
SYNLETT, 2017, 28 (12) :1463-1466