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

[1] ALKYLATION OF THE ISOQUINOLINE SKELETON IN THE 1-POSITION - LITHIATED 2-PIVALOYL AND 2-BIS(DIMETHYLAMINO)-PHOSPHINOYL-1,2,3,4-TETRAHYDROISOQUINOLINES
SEEBACH, D
LOHMANN, JJ
SYFRIG, MA
YOSHIFUJI, M
TETRAHEDRON, 1983, 39 (12) : 1963 - 1974
[2] SYNTHESIS AND STRUCTURE ACTIVITY RELATIONSHIP STUDIES OF A SERIES OF 1,2,3,4-TETRAHYDROISOQUINOLINES SUBSTITUTED IN THE 1-POSITION AND OR 3-POSITION
MATZ, JR
DAILEY, MA
MURRAY, RJ
RAY, R
STAGNITTO, M
PALMER, G
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 204 : 67 - MEDI
[3] SYNTHESIS OF 1,2,3,4-TETRAHYDROISOQUINOLINES
KASHDAN, DS
SCHWARTZ, JA
RAPOPORT, H
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13): : 2638 - 2643
[4] INVESTIGATION ON DIASTEREOSELECTIVE C,C-BOND FORMATION IN THE 1-POSITION OF 1,2,3,4-TETRAHYDROISOQUINOLINES .2. EPC-SYNTHESIS OF TETRAHYDROISOQUINOLINES BY DIASTEREOSELECTIVE ALKYLATION AT THE 1-POSITION OF PHENYLALANINE-DERIVED PRECURSORS - SYNTHESIS OF THE ALKALOID (+)-CORLUMINE
HUBER, IMP
SEEBACH, D
HELVETICA CHIMICA ACTA, 1987, 70 (07) : 1944 - 1954
[5] A NEW SYNTHESIS OF 1,2,3,4-TETRAHYDROISOQUINOLINES
BOBBITT, JM
KHANNA, KL
KIELY, JM
CHEMISTRY & INDUSTRY, 1964, (47) : 1950 - 1951
[6] SYNTHESIS OF DEUTERATED 1,2,3,4-TETRAHYDROISOQUINOLINES
MEESE, CO
EBNER, T
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1988, 25 (03): : 335 - 343
[7] NEW SYNTHESIS 1,2,3,4-TETRAHYDROISOQUINOLINES
DEADY, LW
PIRZADA, N
TOPSOM, RD
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (15): : 799 - &
[8] Synthesis of racemic 1,2,3,4-tetrahydroisoquinolines and their resolution
Suna E.
Trapencieris P.
Chemistry of Heterocyclic Compounds, 2000, Kluwer Academic/Plenum Publishers (36) : 287 - 300
[9] Synthesis of racemic 1,2,3,4-tetrahydroisoquinolines and their separation
Suna, E
Trapencieris, P
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2000, (03): : 348 - 361
[10] ISOQUINOLINE DERIVATIVES .8. SYNTHESIS OF 2-ARALKYL-1,2,3,4-TETRAHYDROISOQUINOLINES
MARKARYAN, EA
ARUSTAMY.ZS
VASILYAN, SS
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1973, (05): : 679 - 682

← 1 2 3 4 5 →