[3+2]-Cycloaddition of Azaoxyallyl Cations with Hexahydro-1,3,5-triazines: Access to 4-imidazolidinones

被引:75
作者
Ji, Danqing [1 ]
Sun, Jiangtao [1 ]
机构
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China
基金
中国国家自然科学基金;
关键词
AZA-OXYALLYL CATIONS; DONOR-ACCEPTOR CYCLOPROPANES; CYCLOADDITION REACTIONS; 1,3,5-TRIAZINANES; OXAZOLIDIN-4-ONES; PYRROLOINDOLINES; COMPLEXES; TRIAZINES; DISCOVERY; ALDEHYDES;
D O I
10.1021/acs.orglett.8b00951
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel base-promoted [3 + 2] cycloaddition reaction of azaoxyallyl cations with hexahydro-1,3,5-triazines has been developed, affording 4-imidazolidinones in moderate to good yields under mild reaction conditions. This simple but efficient protocol features cycloaddition of two in situ formed reactive species in the absence of a transition-metal catalyst.
引用
收藏
页码:2745 / 2748
页数:4
相关论文
共 42 条
[1]   Synthesis and Anticonvulsant Activity of Substituted-1,3-diazaspiro[4.5]decan-4-ones [J].
Aboul-Enein, Mohamed Nabil ;
El-Azzouny, Aida Abdel Sattar ;
Saleh, Ola Ahmed ;
Amin, Kamilia Mahmoud ;
Maklad, Yousreya Ali ;
Hassan, Rasha Mohamed .
ARCHIV DER PHARMAZIE, 2015, 348 (08) :575-588
[2]   Access to 4-Oxazolidinones: A (3+2) Cycloaddition Approach [J].
Acharya, Arjun ;
Montes, Karissa ;
Jeffrey, Christopher S. .
ORGANIC LETTERS, 2016, 18 (23) :6082-6085
[3]   Dearomative Indole Cycloaddition Reactions of Aza-Oxyallyl Cationic Intermediates: Modular Access to Pyrroloindolines [J].
Acharya, Arjun ;
Anumandla, Devendar ;
Jeffrey, Christopher S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (47) :14858-14860
[4]   Intramolecular Aza-[4+3] Cycloaddition Reactions of α-Halohydroxamates [J].
Acharya, Arjun ;
Eickhoff, John A. ;
Jeffrey, Christopher S. .
SYNTHESIS-STUTTGART, 2013, 45 (13) :1825-1836
[5]  
Albizu L, 2010, NAT CHEM BIOL, V6, P587, DOI [10.1038/NCHEMBIO.396, 10.1038/nchembio.396]
[6]   Base-controlled [3+3] cycloaddition of isoquinoline N-oxides with azaoxyallyl cations [J].
An, Yuanyuan ;
Xia, Hongguang ;
Wu, Jie .
CHEMICAL COMMUNICATIONS, 2016, 52 (68) :10415-10418
[7]   Trapping the elusive aza-oxyallylic cation: new opportunities in heterocycloaddition chemistry [J].
Barnes, Korry L. ;
Koster, Anna K. ;
Jeffrey, Christopher S. .
TETRAHEDRON LETTERS, 2014, 55 (34) :4690-4696
[8]   A rational approach to the design and synthesis of a new bradykinin B1 receptor antagonist [J].
Bedos, P ;
Amblard, M ;
Subra, G ;
Dodey, P ;
Luccarini, JM ;
Paquet, JL ;
Pruneau, D ;
Aumelas, A ;
Martinez, J .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (12) :2387-2394
[9]   Novel Synthesis and Pharmacological Characterization of NOP Receptor Agonist 8-[(1S,3aS)-2,3,3a,4,5,6-Hexahydro-1H-phenalen-1-yl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (Ro 64-6198) [J].
Chang, Steven D. ;
Brieaddy, Lawrence E. ;
Harvey, Joseph D. ;
Lewin, Anita H. ;
Mascarella, S. Wayne ;
Seltzman, Herbert H. ;
Reddy, P. Anantha ;
Decker, Ann M. ;
McElhinny, Charles J., Jr. ;
Zhong, Desong ;
Peterson, Elisha E. ;
Navarro, Hernan A. ;
Bruchas, Michael R. ;
Carroll, F. Ivy .
ACS CHEMICAL NEUROSCIENCE, 2015, 6 (12) :1956-1964
[10]   Synthesis and SAR study of diphenylbutylpiperidines as cell autophagy inducers [J].
Chen, Gang ;
Xia, Hongguang ;
Cai, Yu ;
Ma, Dawei ;
Yuan, Junying ;
Yuan, Chengye .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (01) :234-239