Preparation of 4-substituted 10-ethylphenothiazines

被引:6
作者
Ebdrup, S
Jensen, MS
Vedso, P
机构
[1] Novo Nordisk AS, DK-2760 Malov, Denmark
[2] Royal Danish Sch Pharm, Dept Med Chem, DK-2100 Copenhagen, Denmark
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 02期
关键词
D O I
10.1039/a704120i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Under appropriate reaction conditions 10-ethylphenothiazine 1 undergoes lithiation at C-4 using an excess of sec-butyllithium-N,N,N',N'-tetramethyl in diethyl ether, Reaction of the lithiated intermediate with a variety of carbon, halogen, sulfur and silicon electrophiles affords several new 4-substituted 10-ethylphenothiazines 3a-i in good yields.
引用
收藏
页码:351 / 354
页数:4
相关论文
共 19 条
[1]   SOME PHENOTHIAZINE DERIVATIVES - THE COURSE OF THE FRIEDEL CRAFTS REACTION [J].
BALTZLY, R ;
HARFENIST, M ;
WEBB, FJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1946, 68 (12) :2673-2678
[3]  
BOURDILLON C, 1993, J AM CHEM SOC, V115, P2
[4]  
CAUQUIL G, 1960, B SOC CHIM FR, P1049
[5]   The metalation of 10-phenylphenothiazine and of 10-ethylphenothiazine [J].
Gilman, H ;
Van Ess, PR ;
Shirley, DA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 :1214-1216
[6]   The metalation of phenothiazine [J].
Gilman, H ;
Shirley, DA ;
Van Ess, PR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 :625-627
[7]   ACYLATIONS OF 1,10-DILITHIOPHENOTHIAZINE - A NEW SYNTHESIS OF 1-FORMYLPHENOTHIAZINE [J].
HALLBERG, A ;
MARTIN, A .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (02) :433-435
[8]   1,2-DIDEHYDROPHENOTHIAZINES - PREPARATION OF 1-ALKYL AND 1-ARYL-SUBSTITUTED PHENOTHIAZINES BY LITHIUM-DIRECTED ALKYLATION [J].
HALLBERG, A ;
DUNBAR, P ;
HINTERMEISTER, NM ;
SVENSSON, A ;
MARTIN, AR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (05) :969-971
[9]   A NEW SYNTHESIS OF 1-CHLOROPHENOTHIAZINE [J].
HALLBERG, A ;
MARTIN, AR .
SYNTHETIC COMMUNICATIONS, 1983, 13 (06) :467-470
[10]   ON THE ASSIGNMENT OF THE C-13-NMR SPECTRUM OF PHENOTHIAZINE [J].
HALLBERG, A ;
ALSHOWAIER, I ;
MARTIN, AR .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (05) :1435-1436