Synthesis of 3,6-Divinyl-1,2,4,5-Tetrazine, the First Member of the Elusive Vinyltetrazine Family

被引:5
作者
Pican, Stephanie [1 ]
Lapinte, Vincent [1 ,3 ]
Pilard, Jean-Francois [1 ]
Pasquinet, Eric [2 ]
Beller, Lionel [2 ]
Fontaine, Laurent [1 ]
Poullain, Didier [2 ]
机构
[1] Univ Maine, CNRS, UMR6011, UCO2M Chim Polymeres, F-72085 Le Mans 09, France
[2] LE RIPAULT, DAM, CEA, F-37260 Monts, France
[3] Univ Montpellier 2, CNRS, UMR5253, IAM,Inst Charles Gerhardt Montpellier, F-34095 Montpellier 5, France
关键词
azo compounds; condensation; cyclizations; fused ring systems; heterocycles; DIELS-ALDER REACTIONS; SUBSTITUTED TETRAZINES; ANTITUMOR-ACTIVITY; SULFONES; 1,2,4,5-TETRAZINES; DERIVATIVES; CYCLOADDITIONS; BASE;
D O I
10.1055/s-0028-1087818
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the first vinyltetrazine derivative is described. 3,6-Divinyl-1,2,4,5-tetrazine was obtained following a methodology involving cyclization from ail imidate and use of 2-phenylsulfonylethyl groups as masked vinyl entities. The first properties of this unique compound are reported.
引用
收藏
页码:731 / 734
页数:4
相关论文
共 49 条
[1]   Copper(I)-promoted palladium-catalyzed cross-coupling of unsaturated tri-n-butylstannane with heteroaromatic thioether [J].
Alphonse, FA ;
Suzenet, F ;
Keromnes, A ;
Lebret, B ;
Guillaumet, G .
ORGANIC LETTERS, 2003, 5 (06) :803-805
[2]  
American Cyanamid Co, 1958, US Pat., Patent No. [2,845,422, 2845422]
[3]  
Attaryan O.S., 1986, ARM KHIM ZH, V39, P630
[4]   Synthesis of new substituted tetrazines:: electrochemical and spectroscopic properties [J].
Audebert, P ;
Sadki, S ;
Miomandre, F ;
Clavier, G ;
Vernières, MC ;
Saoud, M ;
Hapiot, P .
NEW JOURNAL OF CHEMISTRY, 2004, 28 (03) :387-392
[5]   First example of an electroactive polymer issued from an oligothiophene substituted tetrazine [J].
Audebert, P ;
Sadki, S ;
Miomandre, F ;
Clavier, G .
ELECTROCHEMISTRY COMMUNICATIONS, 2004, 6 (02) :144-147
[6]   Alkene synthesis: elimination of arenesulfinic acid from alkyl aryl sulfones using potassium trimethylsilanolate as base [J].
Baker-Glenn, CAG ;
Barrett, AGM ;
Gray, AA ;
Procopiou, PA ;
Ruston, M .
TETRAHEDRON LETTERS, 2005, 46 (43) :7427-7430
[7]   A DETAILED, CONVENIENT PREPARATION OF DIMETHYL "1,2,4,5-TETRAZINE-3,6-DICARBOXYLATE [J].
BOGER, DL ;
COLEMAN, RS ;
PANEK, JS ;
HUBER, FX ;
SAUER, J .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5377-5379
[8]   SYNTHESIS OF 2-(2-IMIDAZOLINYL) SUBSTITUTED 2,3-DIHYDRO-4H-1,4-BENZOTHIAZINE AND 3,4-DIHYDRO-2H-1,4-BENZOXAZINES [J].
BUTLER, RCM ;
CHAPLEO, CB ;
MYERS, PL ;
WELBOURN, AP .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (01) :177-181
[9]   Novel high-nitrogen materials based on nitroguanyl-substituted tetrazines [J].
Chavez, DE ;
Hiskey, MA ;
Gilardi, RD .
ORGANIC LETTERS, 2004, 6 (17) :2889-2891
[10]  
Chavez DE, 2000, ANGEW CHEM INT EDIT, V39, P1791, DOI 10.1002/(SICI)1521-3773(20000515)39:10<1791::AID-ANIE1791>3.0.CO