ALKYLATION OF N-BOC-1,2,3,4-TETRAHYDROISOQUINOLINES IN THE 1-POSITION AND ITS APPLICATION TO THE SYNTHESIS OF ISOQUINOLINE ALKALOIDS

被引：20

作者：

COPPOLA, GM

机构：

[1] Sandoz Research Institute, Chemistry Research Department, Sandoz Pharmaceuticals Corporation, East Hanover, New Jersey, 07936

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1991年 / 28卷 / 07期

关键词：

D O I：

10.1002/jhet.5570280720

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Boc-protected 1,2,3,4-tetrahydroisoquinolines 2 can be lithiated with t-butyllithium in the presence of N,N,N',N'-tetramethylethylenediamine. Reaction of the anion with alkyl halides provides 1-alkyl N-Boc-1,2,3,4-tetrahydroisoquinolines in 67-71% yield. The protecting group is easily removed in high yield with trifluoroacetic acid. The alkaloids salsolidine (8) and laudanosine (11) were synthesized in racemic form using this method.

引用

页码：1769 / 1772

页数：4

共 50 条

[41] Synthesis of 1,2,3,4-tetrahydroisoquinolines containing electron-withdrawing groups
Quallich, GJ
Makowski, TW
Sanders, AF
Urban, FJ
Vazquez, E
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12): : 4116 - 4119
[42] CONFORMATIONAL-ANALYSIS AND MOLECULAR MODELING OF 1-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINES, 4-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINES, AND 1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINES AS D1 DOPAMINE RECEPTOR LIGANDS
CHARIFSON, PS
BOWEN, JP
WYRICK, SD
HOFFMAN, AJ
CORY, M
MCPHAIL, AT
MAILMAN, RB
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (09) : 2050 - 2058
[43] SYNTHESIS OF ISOQUINOLINES .X. 1-ALKYL-1,2,3,4-TETRAHYDROISOQUINOLINES
BOBBITT, JM
STEINFEL.AS
WEISGRAB.KH
DUTTA, S
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (08): : 2478 - &
[44] Synthesis of 6,7-dimethoxy-1-halobenzyl-1,2,3,4-tetrahydroisoquinolines
Cho, SD
Kweon, DH
Kang, YJ
Lee, SG
Lee, WS
Yoon, YJ
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (05) : 1151 - 1156
[45] A facile synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinolines
Hu, Min
Guzzo, Peter R.
Zha, Congxiang
Nacro, Kassoum
Yang, Yuh-Lin
Hassler, Carla
Liu, Shuang
TETRAHEDRON LETTERS, 2012, 53 (07) : 846 - 848
[46] AN EFFICIENT SYNTHESIS OF 4-ARYL-1,2,3,4-TETRAHYDROISOQUINOLINES
NARASIMHAN, NS
PATIL, PA
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (03) : 191 - 192
[47] A NEW SYNTHESIS OF 4-OXO-1,2,3,4-TETRAHYDROISOQUINOLINES
HARCOURT, DN
WAIGH, RD
CHEMICAL COMMUNICATIONS, 1968, (12) : 692 - &
[48] ASYMMETRIC ALKYLATION OF ALPHA-AMINO CARBANIONS - AN ENANTIOSELECTIVE SYNTHESIS OF (S)-1-ALKYL-1,2,3,4-TETRAHYDROISOQUINOLINES
MEYERS, AI
FUENTES, LM
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (01) : 117 - 118
[49] NEW METHOD FOR SYNTHESIS OF 2-ACYL-1-ARYL-1,2,3,4-TETRAHYDROISOQUINOLINES
MOLLOV, NM
VENKOV, AP
SYNTHESIS-STUTTGART, 1978, (01): : 62 - 63
[50] Synthesis of 1,2,3,4-tetrahydroisoquinolines containing electron withdrawing groups.
Quallich, GJ
Makowski, TW
Sanders, AF
Urban, FJ
Vazquez, E
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 324 - ORGN

← 1 2 3 4 5 →