One-Pot Three-Component Strategy for Functionalized 2-Aminoimidazoles via Ring Opening of α-Nitro Epoxides

被引:29
作者
Guo, Xiao [1 ]
Chen, Wenteng [1 ]
Chen, Binhui [1 ]
Huang, Wei [1 ]
Qi, Weixing [1 ]
Zhang, Guolin [1 ]
Yu, Yongping [1 ]
机构
[1] Zhejiang Univ, Coll Pharmaceut Sci, Zhejiang Prov Key Lab Anticanc Drug Res, Hangzhou 310058, Zhejiang, Peoples R China
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
NITROEPOXIDES;
D O I
10.1021/acs.orglett.5b00289
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Functionalized 2-aminoimidazole derivatives have been synthesized via a three-component domino reaction of a-nitroepoxides and cyanamide with a series of amines under mild conditions without the need for any additives. This reaction represents a practical process for the facile conversion of a-nitroepoxides to 2-aminoimidazoles via ring opening of epoxides.
引用
收藏
页码:1157 / 1159
页数:3
相关论文
共 23 条
[1]   Dynamic Kinetic Asymmetric Ring-Opening/Reductive Amination Sequence of Racemic Nitroepoxides with Chiral Amines: Enantioselective Synthesis of Chiral Vicinal Diamines [J].
Agut, Juan ;
Vidal, Andreu ;
Rodriguez, Santiago ;
Gonzalez, Florenci V. .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (11) :5717-5722
[2]   Regioselective Functionalization of the Imidazole Ring via Transition Metal-Catalyzed C-N and C-C Bond Forming Reactions [J].
Bellina, Fabio ;
Rossi, Renzo .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (08) :1223-1276
[3]   The chemistry and biology of organic guanidine derivatives [J].
Berlinck, Roberto G. S. ;
Trindade-Silva, Amaro E. ;
Santos, Mario F. C. .
NATURAL PRODUCT REPORTS, 2012, 29 (12) :1382-1406
[4]   SYNTHESIS OF 1-ALKYL-2-NITROIMIDAZOLE-5-CARBOXALDEHYDES [J].
CAVALLERI, B ;
BALLOTTA, R ;
LANCINI, GC .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1972, 9 (05) :979-+
[5]   Clinical Practice Guidelines for Clostridium difficile Infection in Adults: 2010 Update by the Society for Healthcare Epidemiology of America (SHEA) and the Infectious Diseases Society of America (IDSA) [J].
Cohen, Stuart H. ;
Gerding, Dale N. ;
Johnson, Stuart ;
Kelly, Ciaran P. ;
Loo, Vivian G. ;
McDonald, L. Clifford ;
Pepin, Jacques ;
Wilcox, Mark H. .
INFECTION CONTROL AND HOSPITAL EPIDEMIOLOGY, 2010, 31 (05) :431-455
[6]  
De Luca L, 2006, CURR MED CHEM, V13, P1
[7]  
Eicher T., 2003, CHEM HETEROCYCLES
[8]   Concise and Diversity-Oriented Route toward Polysubstituted 2-Aminoimidazole Alkaloids and Their Analogues [J].
Ermolat'ev, Denis S. ;
Bariwal, Jitender B. ;
Steenackers, Hans P. L. ;
De Keersmaecker, Sigrid C. J. ;
Van der Eycken, Erik V. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (49) :9465-9468
[9]   Synthesis of the Reported Structures for Kealiinines B and C [J].
Gibbons, Joseph B. ;
Gligorich, Keith M. ;
Welm, Bryan E. ;
Looper, Ryan E. .
ORGANIC LETTERS, 2012, 14 (18) :4734-4737
[10]   Addition-Hydroamination Reactions of Propargyl Cyanamides: Rapid Access to Highly Substituted 2-Aminoimidazoles [J].
Giles, Robert L. ;
Sullivan, John D. ;
Steiner, Andrew M. ;
Looper, Ryan E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (17) :3116-3120