PREPARATION, REACTIVITY AND SYNTHETIC APPLICATIONS OF BIS(IMINOPHOSPHORANES) - NEW ENTRIES TO FUSED 1,3,5-BENZOTRIAZEPINES, 1,3-BENZODIAZEPINES AND INDOLE-DERIVATIVES

被引:23
作者
MOLINA, P [1 ]
ARQUES, A [1 ]
ALIAS, A [1 ]
VINADER, MV [1 ]
FOCESFOCES, MC [1 ]
HERNANDEZCANO, F [1 ]
机构
[1] CSIC,INST QUIM FISICA ROCASOLANO,UEI CRISTALOGRAFIA,E-28006 MADRID,SPAIN
关键词
BIS(IMINOPHOSPHORANES); AZA WITTIG-TYPE REACTION; FUSED 1,3,5-BENZOTRIAZEPINES; 1,3-BENZODIAZEPINES; INDOLE DERIVATIVES;
D O I
10.1016/S0040-4020(01)92251-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An aza-Wittig-type reaction of bis(iminophosphorane) 2 with two moles of alkyl or aryl iso(thio)cyanates leads to indazolo[2'3':1,5][1,2,4]triazolo[4,3-a][1,3,5]benzotriazepines 7. The bis(iminophosphorane) 4 reacts with aromatic iso(thio)cyanates to give the corresponding iminophosphoranes 13 derived from the indole ring. Compound 4 also reacts with acyl chlorides to give [1,3]-benzodiazepines 19. The crystal structure of compound 13c has been determined.
引用
收藏
页码:3091 / 3110
页数:20
相关论文
共 34 条
[1]   NUCLEAR MAGNETIC-RESONANCE STUDIES .6. PROPERTIES OF PHOSPHORUS-NITROGEN YLIDES [J].
ALBRIGHT, TA ;
FREEMAN, WJ ;
SCHWEIZER, EE .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (16) :2716-2720
[2]  
ALLINGER NL, 1971, TETRAHEDRON LETT, P3259
[3]  
[Anonymous], 1974, INT TABLES XRAY CRYS, VIV
[4]   1H-INDAZOLE AND 2H-INDAZOLE BY THERMAL AND PHOTOLYTIC DECOMPOSITION OF ORTHO-AZIDOBENZOIC ACID AND ORTHO-AZIDOBENZALDEHYDE DERIVATIVES [J].
ARDAKANI, MA ;
SMALLEY, RK ;
SMITH, RH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (10) :2501-2506
[5]   REACTIVITY OF IMINOPHOSPHORANES TOWARDS SOME SYMMETRICAL DICARBONYL DICHLORIDES - SYNTHESES AND MECHANISMS [J].
AUBERT, T ;
FARNIER, M ;
GUILARD, R .
TETRAHEDRON, 1991, 47 (01) :53-60
[6]   SYNTHESIS OF REACTIVITY OF LAMBDA-5-PHOSPHAZENES - USES AS SYNTHETIC INTERMEDIATES [J].
BARLUENGA, J ;
PALACIOS, F .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1991, 23 (01) :1-65
[7]  
BASSET A, 1990, TETRAHEDRON LETT, P6561
[8]   NMR-STUDIES IN THE HETEROCYCLIC SERIES .31. EFFECT OF N-SUBSTITUENTS ON THE C-13 NMR PARAMETERS OF AZOLES [J].
BEGTRUP, M ;
ELGUERO, J ;
FAURE, R ;
CAMPS, P ;
ESTOPA, C ;
ILAVSKY, D ;
FRUCHIER, A ;
MARZIN, C ;
DEMENDOZA, J .
MAGNETIC RESONANCE IN CHEMISTRY, 1988, 26 (02) :134-151
[9]   REACTIONS OF ORTHO-PHENYLENEDIAMINE AND SOME IMINOPHOSPHORANE DERIVATIVES WITH DIMETHYL ACETYLENEDICARBOXYLATE [J].
BRIGGS, EM ;
BROWN, GW ;
DAWSON, WT ;
JIRICNY, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (15) :641-642
[10]  
BURSON WC, 1991, SYNTHESIS-STUTTGART, P475