A SIMPLE PREPARATION OF 1H-1,4-DIAZEPINE-7(6H)-THIONES AND THEIR RING CONTRACTION TO 1-VINYL-2,3-DIHYDRO-1H-IMIDAZOLE-2-THIONES BY THERMAL REARRANGEMENT REACTION

被引:0
作者
BARLUENGA, J [1 ]
CARLON, RP [1 ]
GONZALEZ, J [1 ]
JOGLAR, J [1 ]
ORTIZ, FL [1 ]
FUSTERO, S [1 ]
机构
[1] UNIV VALENCIA,FAC FARM,DEPT QUIM ORGAN,E-46010 VALENCIA,SPAIN
来源
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE | 1992年 / 129卷 / 06期
关键词
2-AZA-1,3-DIENES; 4+2] CYCLOADDITION REACTION; 1,2-DIHYDROPYRIDINE-4(3H)-THIONES; 1H-1,4-DIAZEPINE-7(6H)-THIONES; 1-VINYL-3H-IMIDAZOLE-2(3H)-THIONES; N-15; NMR; NOE; COLOC; HMBC; 3-21G-ASTERISK-CALCULATIONS;
D O I
暂无
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
An efficient synthesis of 1H-1,4-diazepine-7(6H)-thiones via a tandem [4+2]-cycloaddition-ring expansion of chlorinated 2-aza-1,3-dienes with trimethylsilyl isothiocyanate is described. A thermal rearrangement of these 1,4-diazepine derivatives to 1-vinylimidazole-2(3H)-thiones has also been found. The structure all of these compounds was determined using a combination of modern NMR methods.
引用
收藏
页码:566 / 578
页数:13
相关论文
共 43 条
[1]  
ANET FAL, 1975, DYNAMIC NUCLEAR MAGN, P543
[2]  
BARCHET R, 1964, TETRAHEDRON LETT, P2239
[3]   UNACTIVATED 2-AZA-1,3-DIENES - HALOGENATION AND FACE SELECTIVITY IN DIELS-ALDER REACTIONS [J].
BARLUENGA, J ;
GONZALEZ, FJ ;
FUSTERO, S .
TETRAHEDRON LETTERS, 1990, 31 (03) :397-398
[4]   CYCLO-ADDITION OF UNACTIVATED 2-AZA-1,3-DIENES WITH HETEROCUMULENES - A CONVENIENT ROUTE TO THE SYNTHESIS OF 1,3-DIFUNCTIONALIZED COMPOUNDS [J].
BARLUENGA, J ;
GONZALEZ, FJ ;
GOTOR, V ;
FUSTERO, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07) :1739-1744
[5]   TANDEM CYCLOADDITION REARRANGEMENT OF 2-AZA-1,3-DIENES - A SIMPLE AND EFFICIENT SYNTHESIS OF 1H-1,4-DIAZEPINE-7(6H)-THIONES [J].
BARLUENGA, J ;
CARLON, RP ;
GONZALEZ, FJ ;
ORTIZ, FL ;
FUSTERO, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (23) :1704-1705
[6]  
BARLUENGA J, 1990, SYNLETT, P129
[7]   SYNTHESIS AND DIASTEREOFACIAL SELECTIVITY IN DIELS-ALDER REACTIONS OF HALOGENATED 2-AZA 1,3-DIENES [J].
BARLUENGA, J ;
GONZALEZ, FJ ;
FUSTERO, S ;
GARCIAGRANDA, S ;
PEREZCARRENO, E .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) :4459-4463
[8]   A NEW CLASS OF FUSED 1,4-DIAZEPINES - SYNTHESIS OF SUBSTITUTED 8,8A-DIHYDROFURO[2,3-B][1,4]DIAZEPIN-2-ONES [J].
BARLUENGA, J ;
TOMAS, M ;
BALLESTEROS, A ;
KONG, JS ;
GRANDA, SG ;
PEREZCARRENO, E .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (06) :353-354
[9]   CORRELATION OF PROTON AND N-15 CHEMICAL-SHIFTS BY MULTIPLE QUANTUM NMR [J].
BAX, A ;
GRIFFEY, RH ;
HAWKINS, BL .
JOURNAL OF MAGNETIC RESONANCE, 1983, 55 (02) :301-315
[10]   H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].
BAX, A ;
SUMMERS, MF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2093-2094