SYNTHETIC APPLICATIONS OF BIS(IMINOPHOSPHORANES) - ONE-POT PREPARATION OF RIGID BICYCLIC GUANIDINES

被引:48
作者
MOLINA, P
ALAJARIN, M
VIDAL, A
机构
[1] Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, E-30071, Murcia, Campus de Espinardo
关键词
D O I
10.1021/jo00059a015
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A one-pot synthesis of [6 + 6], [6 + 7], and [6 + 8] bicyclic guanidines based on a new method of dihydropyrimido annelation, which involves reaction of bis(iminophosphoranes) with aryl isocyanates or isothiocyanates is described. The method is also applicable for the preparation of chiral bicyclic guanidines.
引用
收藏
页码:1687 / 1695
页数:9
相关论文
共 33 条
[11]   CHIRAL RECOGNITION OF AROMATIC CARBOXYLATE ANIONS BY AN OPTICALLY-ACTIVE ABIOTIC RECEPTOR CONTAINING A RIGID GUANIDINIUM BINDING SUBUNIT [J].
ECHAVARREN, A ;
GALAN, A ;
LEHN, JM ;
DEMENDOZA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) :4994-4995
[12]   ANION-RECEPTOR MOLECULES - SYNTHESIS OF A CHIRAL AND FUNCTIONALIZED BINDING SUBUNIT, A BICYCLIC GUANIDINIUM GROUP DERIVED FROM L-ASPARAGINE OR D-ASPARAGINE [J].
ECHAVARREN, A ;
GALAN, A ;
DEMENDOZA, J ;
SALMERON, A ;
LEHN, JM .
HELVETICA CHIMICA ACTA, 1988, 71 (04) :685-693
[13]  
ESSER F, 1987, SYNTHESIS-STUTTGART, P460
[14]   MASS-SPECTROMETRY OF SOME AROMATIC AZIDES [J].
FRASER, RTM ;
PAUL, NC ;
BAGLEY, MJ .
ORGANIC MASS SPECTROMETRY, 1973, 7 (01) :83-88
[15]   A SYNTHETIC RECEPTOR FOR DINUCLEOTIDES [J].
GALAN, A ;
DEMENDOZA, J ;
TOIRON, C ;
BRUIX, M ;
DESLONGCHAMPS, G ;
REBEK, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) :9424-9425
[16]  
HUISGEN R, 1969, CHEM BER, V102, P1948
[17]  
KAO YS, 1956, HUA HSUEH PAO, V22, P32
[18]   PTILOMYCALIN-A - A NOVEL POLYCYCLIC GUANIDINE ALKALOID OF MARINE ORIGIN [J].
KASHMAN, Y ;
HIRSH, S ;
MCCONNELL, OJ ;
OHTANI, I ;
KUSUMI, T ;
KAKISAWA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) :8925-8926
[19]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[20]   PREPARATION OF FUSED [1,3,5]BENZOTRIAZEPINES BY A TANDEM AZA WITTIG CARBODIIMIDE-MEDIATED ANNELATION REACTION [J].
MOLINA, P ;
ARQUES, A ;
ALIAS, A .
TETRAHEDRON LETTERS, 1991, 32 (25) :2979-2982