Aza-annulation as a versatile approach to the synthesis of non-benzodiazepene compounds for the treatment of sleep disorders

被引：24
作者：
Benovsky, P
Stille, JR
机构：
[1] ELI LILLY & CO,LILLY RES LABS,CHEM PROC RES & DEV,INDIANAPOLIS,IN 46285
[2] MICHIGAN STATE UNIV,DEPT CHEM,E LANSING,MI 48824
来源：
TETRAHEDRON LETTERS | 1997年 / 38卷 / 49期
基金：
美国国家卫生研究院; 美国国家科学基金会;
关键词：
D O I：
10.1016/S0040-4039(97)10297-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The aza-annulation of enamino ester substrates has been demonstrated as an efficient alternative to the syntheses of non-benzodiazepine sleep inducers. Enamino ester substrates derived from aryl, thiophene, and indole functionality were prepared from the corresponding ethyl amines by isothiocyanate formation followed by acid catalyzed cyclization. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：8475 / 8478
页数：4
相关论文
共 31 条
[1]   ASYMMETRIC FORMATION OF QUATERNARY CENTERS THROUGH AZA-ANNULATION OF CHIRAL BETA-ENAMINO ESTERS WITH ACRYLATE DERIVATIVES [J].
BARTA, NS ;
BRODE, A ;
STILLE, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) :6201-6206
[2]   Formation of dihydropyridone- and pyridone-based peptide analogs through aza-annulation of beta-enamino ester and amide substrates with alpha-amido acrylate derivatives [J].
Beholz, LG ;
Benovsky, P ;
Ward, DL ;
Barta, NS ;
Stille, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) :1033-1042
[3]  
BHATTACHARJYA A, 1983, HETEROCYCLES, V20, P2397
[4]   IMINE-ENAMINE ANNELATION - STEREOSELECTIVE SYNTHESES OF (+/-)-DEPLANCHEINE [J].
CALABI, L ;
DANIELI, B ;
LESMA, G ;
PALMISANO, G .
TETRAHEDRON LETTERS, 1982, 23 (20) :2139-2142
[5]   AZA-ANNULATION AS A ROUTE TO HYDROXYLATED ALKALOID LIPIDS - THE SYNTHESIS OF (+/-)-PROSOPININE [J].
COOK, GR ;
BEHOLZ, LG ;
STILLE, JR .
TETRAHEDRON LETTERS, 1994, 35 (11) :1669-1672
[6]   CONSTRUCTION OF HYDROXYLATED ALKALOIDS (+/-)-MANNONOLACTAM, (+/-)-DEOXYMANNOJIRIMYCIN, AND (+/-)-PROSOPININE THROUGH AZA-ANNULATION [J].
COOK, GR ;
BEHOLZ, LG ;
STILLE, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) :3575-3584
[7]  
DANIELI B, 1981, GAZZ CHIM ITAL, V111, P257
[8]   EFFICIENT SYNTHESIS OF 1-ETHYL-2,3,4,6,7,12-HEXAHYDROINDOLO[2,3-A]QUINOLIZINE - KEY PRECURSOR TO EBURNANE ALKALOIDS [J].
DANIELI, B ;
LESMA, G ;
PALMISANO, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (03) :109-109
[9]  
DANIELI B, 1984, SYNTHESIS-STUTTGART, P353
[10]   TRICYCLIC PYRIDINE-DERIVATIVES WITH HIGH-AFFINITY TO THE CENTRAL BENZODIAZEPINE RECEPTOR [J].
FISCHER, U ;
MOHLER, H ;
SCHNEIDER, F ;
WIDMER, U .
HELVETICA CHIMICA ACTA, 1990, 73 (04) :763-781
1234