Base-promoted cascade reaction of isocyanides, selenium and amines: a practical approach to 2-aminobenzo[d][1,3] selenazines under metal-free conditions

被引:41
作者
Fang, Yi [1 ]
Wang, Shun-Yi
Shen, Xiao-Bin
Ji, Shun-Jun
机构
[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China
基金
中国国家自然科学基金;
关键词
SAFETY-CATCH LINKERS; MULTICOMPONENT REACTIONS; RADICAL TRIFLUOROMETHYLATION; PHENANTHRIDINE DERIVATIVES; CONTAINING HETEROCYCLES; OXIDATIVE CYCLIZATION; ORGANOSELENIUM; EBSELEN; CHEMISTRY; ISOSELENOCYANATES;
D O I
10.1039/c5qo00150a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
new practical approach for constructing 2-aminobenzo[d][1,3] selenazines by base mediated multicomponent reaction of isocyanides, selenium and amines under metal-free conditions is reported. A series of selenazine derivatives are observed in moderate to excellent yields.
引用
收藏
页码:1338 / 1341
页数:4
相关论文
共 75 条
[31]  
KALAI T, 1995, SYNTHESIS-STUTTGART, P1278
[32]   Selenocyclizations: Control by coordination and by the counterion [J].
Khokhar, SS ;
Wirth, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) :631-633
[33]   Efficient synthesis of selenoureas from the corresponding carbodiimides [J].
Koketsu, M ;
Takakura, N ;
Ishihara, I .
SYNTHETIC COMMUNICATIONS, 2002, 32 (19) :3075-3079
[34]   Synthesis of 1,3-selenazines and 1,3-selenazolidines via intramolecular addition of N-allylselenoureas [J].
Koketsu, Mamoru ;
Kiyokuni, Takashi ;
Sakai, Tsutomu ;
Ando, Hiromune ;
Ishihara, Hideharu .
CHEMISTRY LETTERS, 2006, 35 (06) :626-627
[35]  
LEVSHIN I B, 1981, Pharmaceutical Chemistry Journal (English Translation of Khimiko-Farmatsevticheskii Zhurnal), V15, P242, DOI 10.1007/BF00762895
[36]   Direct Annulations toward Phosphorylated Oxindoles: Silver-Catalyzed Carbon-Phosphorus Functionalization of Alkenes [J].
Li, Ya-Min ;
Sun, Meng ;
Wang, Hong-Li ;
Tian, Qiu-Ping ;
Yang, Shang-Dong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) :3972-3976
[37]   PREPARATION AND PROPERTIES OF SOME THIOURONIUM FLUORENYLIDES AND CYCLOPENTADIENYLIDES AND ATTEMPTED PREPARATION OF SELENOURONIUM AND GUANIDINIUM FLUORENYLIDES [J].
LLOYD, D ;
MILLAR, RW ;
LUMBROSO, H ;
LIEGEOIS, C .
TETRAHEDRON, 1977, 33 (11) :1379-1389
[38]   N-thio- and N-selenophenacylamidines:: electrophilic activation as a route to some 1-hetero-3-aza-4-dimethylaminobuta-1,3-dienes [J].
Manh, GT ;
Purseigle, F ;
Dubreuil, D ;
Pradère, JP ;
Guingant, A ;
Danion-Bougot, R ;
Danion, D ;
Toupet, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (19) :2821-2828
[39]   ANTITUMOR-ACTIVITY OF BIS(DIPHENYLPHOSPHINO)ALKANES, THEIR GOLD(I) COORDINATION-COMPLEXES, AND RELATED-COMPOUNDS [J].
MIRABELLI, CK ;
HILL, DT ;
FAUCETTE, LF ;
MCCABE, FL ;
GIRARD, GR ;
BRYAN, DB ;
SUTTON, BM ;
BARTUS, JO ;
CROOKE, ST ;
JOHNSON, RK .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (12) :2181-2190
[40]   Chemistry of biologically important synthetic organoselenium compounds [J].
Mugesh, G ;
du Mont, WW ;
Sies, H .
CHEMICAL REVIEWS, 2001, 101 (07) :2125-2179