MODIFICATION OF THE PICTET-SPENGLER REACTION IN THE SYNTHESIS OF FUSED 2,3-BENZODIAZOCINES

被引:2
作者
Tolkunov, A. S. [1 ]
Baumer, V. N. [2 ]
Palamarchuk, G. V. [2 ]
Shishkin, O. V. [2 ,3 ]
Mazepa, A. V. [4 ]
Tolkunov, S. V. [1 ]
Bogza, S. L. [1 ]
机构
[1] Natl Acad Sci Ukraine, LM Litvinenko Inst Phys Organ Chem & Coal Chem, UA-83114 Donetsk, Ukraine
[2] Natl Acad Sci Ukraine, Inst Single Crystals, Res Branch Chem Funct Mat, UA-61001 Kharkov, Ukraine
[3] Kharkov Natl Univ, UA-61077 Kharkov, Ukraine
[4] Natl Acad Sci Ukraine, AV Bogatsky Physicochem Inst, UA-65080 Odessa, Ukraine
关键词
3-amino-2-[2-(3,4-dimethoxyphenyl)ethyl]quinazolin-4(3H)-one; fused diazocines; hydrochloric acid; tetrahydroquinazolino[3,2-c][2,3]benzodiazocin-15-ones; trifluoroacetic acid; cyclization; Pictet-Spengler reaction; N-NITRENES; INTRAMOLECULAR REACTIONS; DERIVATIVES; ALKENES;
D O I
10.1007/s10593-011-0867-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new strategy for the synthesis of the eight-membered heterocyclic skeleton of tetrahydroquinazolino[3,2-c][2,3]benzodiazocin-15-ones, based on the Pictet-Spengler reaction of 3-amino-2-[2-(3,4-dimethoxyphenyl)ethyl]quinazolin-4(3H)-one with carbonyl compounds in acidic media, is proposed.
引用
收藏
页码:1006 / 1013
页数:8
相关论文
共 16 条
[1]   SYNTHESIS OF POLYNUCLEAR HETEROCYCLES .4. "IMIDAZO[4,5-G][3,1]-BENZOXAZINONES, IMIDAZO[4,5-G]QUINAZOLINONES, IMIDAZO[4,5-G]QUINAZOLINEDIONES, AND IMIDAZO[4,5-F]INDAZOLINONES [J].
ALKHADER, MA ;
PERERA, RC ;
SINHA, RP ;
SMALLEY, RK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (04) :1056-1062
[2]   AROMATIC AND PSEUDOAROMATIC NONBENZENOID SYSTEMS .2. STUDIES DIRECTED TOWARD THE 1,2-DIAZA-3,5,7-CYCLOOCTATRIENE SYSTEM [J].
ALLINGER, NL ;
YOUNGDALE, GA .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (09) :1509-1511
[3]  
Atkinson R. S., J CHEM SOC CHEM COMM, V1085, P1218
[4]   INTRAMOLECULAR REACTIONS OF N-NITRENES - DESCRIPTION OF THE TRANSITION-STATE GEOMETRY FOR ADDITION TO ALKENES [J].
ATKINSON, RS ;
GRIMSHIRE, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (05) :1135-1145
[5]   AZIRIDINATION BY OXIDATIVE ADDITION OF N-AMINOQUINAZOLONES TO ALKENES - EVIDENCE FOR NON-INVOLVEMENT OF N-NITRENES [J].
ATKINSON, RS ;
GRIMSHIRE, MJ ;
KELLY, BJ .
TETRAHEDRON, 1989, 45 (10) :2875-2886
[6]   INTRAMOLECULAR REACTIONS OF N-NITRENES - OXIDATION OF 3-AMINO-2-(2,4-DIMETHOXYPHENYLPROPYL)QUINAZOLIN-4(3H)-ONE [J].
ATKINSON, RS ;
GAWAD, NA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (02) :341-344
[7]  
Hashash M. A. El-, 1979, REV ROUM CHIM, V23, P1509
[8]   DIAZIRIDINES .5. REACTION OF SOME 1-AROYLDIAZIRIDINES AND 1,2-DIACYLDIAZIRIDINES [J].
HEINE, HW ;
BACLAWSKI, LM ;
BONSER, SM ;
WACHOB, GD .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (20) :3229-3232
[9]   Anxiolytic 2,3-benzodiazepines, their specific binding to the basal ganglia [J].
Horváth, EJ ;
Horváth, K ;
Hámori, T ;
Fekete, MIK ;
Sólyom, S ;
Palkovits, M .
PROGRESS IN NEUROBIOLOGY, 2000, 60 (04) :309-342
[10]   BENZOFURAZAN N-OXIDES AS SYNTHETIC PRECURSORS .3. ACID-CATALYZED CYCLIZATION OF NN-DIALKYL-N'-(O-NITROPHENYL)HYDRAZINES [J].
LATHAM, DWS ;
METHCOHN, O ;
SUSCHITZKY, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (05) :478-483