Facile access to oxazolidin-2-imine, thiazolidin-2-imine and imidazolidin-2-imine derivatives bearing an exocyclic haloalkyliene via direct halocyclization between propargylamines, heterocumulenes and I2 (NBS)

被引:15
作者
Huang, Shujian [1 ]
Shao, Yinlin [1 ]
Liu, Ruiting [1 ]
Zhou, Xigeng [1 ,2 ]
机构
[1] Fudan Univ, Dept Chem, Shanghai Key Lab Mol Catalysis & Innovat Mat, Shanghai 200433, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金; 高等学校博士学科点专项科研基金;
关键词
Heterocycles; Metal-free; Iodocyclization; Propargylamines; CATALYZED CYCLOISOMERIZATIONS; REGIOSELECTIVE SYNTHESIS; SUBSTITUTED IMIDAZOLES; ANTIMICROBIAL ACTIVITY; CYCLIC GUANIDINES; VINYL HALIDES; OXAZOLE; CYCLIZATION; INHIBITORS; ACID;
D O I
10.1016/j.tet.2015.04.080
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, cheap, efficient, and metal-free method for one-step synthesis of a library of 1,3-diheteroatom five-membered heterocycles with exocyclic C=N and C=C double bonds was presented. The convenient reactions proceed via the direct three-component halocyclization of propargylamines, heterocumulenes and I-2 (NBS). (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4219 / 4226
页数:8
相关论文
共 90 条
[21]   Synthesis and Anticancer Activity of All Known (-)-Agelastatin Alkaloids [J].
Han, Sunkyu ;
Siegel, Dustin S. ;
Morrison, Karen C. ;
Hergenrother, Paul J. ;
Movassaghi, Mohammad .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (23) :11970-11984
[22]   Substituted thiazoles VII. Synthesis and antitumor activity of certain 2-(substituted amino)-4-phenyl-1,3-thiazole analogs [J].
Hassan, Ghada S. ;
El-Messery, Shahenda M. ;
Al-Omary, Fatmah A. M. ;
El-Subbagh, Hussein I. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (20) :6318-6323
[23]   Pyrrolidine bis-cyclic guanidines with antimicrobial activity against drug-resistant Gram-positive pathogens identified from a mixture-based combinatorial library [J].
Hensler, Mary E. ;
Bernstein, Gregory ;
Nizet, Victor ;
Nefzi, Adel .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (19) :5073-5079
[24]   Ln[N(SiMe3)2]3-Catalyzed Cross-Diinsertion of CN/CC into an N-H Bond: Facile Synthesis of 1,2,4-Trisubstituted Imidazoles from Propargylamines and Nitriles [J].
Hong, Longcheng ;
Shao, Yinlin ;
Zhang, Lixin ;
Zhou, Xigeng .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (28) :8551-8555
[25]   L1-Medial Skeleton of Point Cloud [J].
Huang, Hui ;
Wu, Shihao ;
Cohen-Or, Daniel ;
Gong, Minglun ;
Zhang, Hao ;
Li, Guiqing ;
Chen, Baoquan .
ACM TRANSACTIONS ON GRAPHICS, 2013, 32 (04)
[26]  
Husain Asif, 2013, J Pharm Bioallied Sci, V5, P154, DOI 10.4103/0975-7406.111822
[27]   Thioamides as useful synthons in the synthesis of heterocycles [J].
Jagodzinski, TS .
CHEMICAL REVIEWS, 2003, 103 (01) :197-227
[28]   Imidazole, oxazole and thiazole alkaloids [J].
Jin, Zhong .
NATURAL PRODUCT REPORTS, 2006, 23 (03) :464-496
[29]   Synthesis and characterization of new metallophthalocyanines bearing highly substituted imidazoles [J].
Karimi, Ali Reza ;
Bayat, Fahimeh .
TETRAHEDRON LETTERS, 2013, 54 (01) :45-48
[30]   Palladium-Catalyzed Catellani Aminocyclopropanation Reactions with Vinyl Halides [J].
Khanna, Avinash ;
Premachandra, Ilandari Dewage Udara Anulal ;
Sung, Paul D. ;
Van Vranken, David L. .
ORGANIC LETTERS, 2013, 15 (12) :3158-3161