PREPARATION OF TETRAHYDROISOQUINOLINES FROM N-(TERT-BUTOXYCARBONYL)-2-METHYLBENZYLAMINES

被引：0
|
作者：
CLARK, RD
JAHANGIR
机构：
来源：
HETEROCYCLES | 1991年 / 32卷 / 09期
关键词：
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Dilithiation of N-(tert-butoxycarbonyl)-2-methylbenzylamine (1a) followed by treatment with N,N-dimethylformamide affords 2-(tert-butoxycarbonyl)-3-hydroxy-tetrahydroisoquinoline (3a). Dehydration and reduction of 3a afford BOC-tetrahydroisoquinoline (5a). The methodology is also applicable to synthesis of chloro and fluoro substituted tetrahydroisoquinolines (5b,c), 3 and 4 substituted derivatives (8,10), and the hexahydro-2H-benzoquinolizine ring system (13).
引用
收藏
页码：1699 / 1703
页数：5
相关论文
共 50 条
  • [1] HETEROATOM-DIRECTED LATERAL LITHIATION - SYNTHESIS OF ISOQUINOLINE DERIVATIVES FROM N-(TERT-BUTOXYCARBONYL)-2-METHYLBENZYLAMINES
    CLARK, RD
    JAHANGIR
    LANGSTON, JA
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (01): : 23 - 30
  • [2] PREPARATION OF INDOLES AND OXINDOLES FROM N-(TERT-BUTOXYCARBONYL)-2-ALKYLANILINES
    CLARK, RD
    MUCHOWSKI, JM
    FISHER, LE
    FLIPPIN, LA
    REPKE, DB
    SOUCHET, M
    SYNTHESIS-STUTTGART, 1991, (10): : 871 - 878
  • [3] N-(tert-butoxycarbonyl)-2-phenylglycine
    GonzalezCameno, AM
    Badia, D
    Dominguez, E
    Arriortua, MI
    Urtiaga, MK
    Solans, X
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 : 3169 - 3171
  • [4] STRUCTURE OF N-(TERT-BUTOXYCARBONYL)GLYCINE
    SEMERTZIDIS, M
    MATSOUKAS, J
    NASTOPOULOS, V
    HONDRELIS, J
    VOLIOTIS, S
    LEBAN, I
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 1989, 45 : 1474 - 1475
  • [5] Preparation of 4-alkyl-2-[N-(tert-butoxycarbonyl)amino]-pyridines by alkylation, nucleophilic addition, and acylation of 2-[N-(tert-butoxycarbonyl)amino]-4-picoline
    Ihle, NC
    Krause, AE
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14): : 4810 - 4811
  • [6] ORTHO FUNCTIONALIZATION OF N-(TERT-BUTOXYCARBONYL)ANILINE
    MUCHOWSKI, JM
    VENUTI, MC
    JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23): : 4798 - 4801
  • [7] Practical one-pot synthesis of N-(tert-butoxycarbonyl)sulfamide from chlorosulfonyl isocyanate via N-(tert-butoxycarbonyl)aminosulfonylpyridinium salt
    Masui, T
    Kabaki, M
    Watanabe, H
    Kobayashi, T
    Masui, Y
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2004, 8 (03) : 408 - 410
  • [8] X-RAY AND IR STUDIES OF N-(TERT-BUTOXYCARBONYL)-L-ALANINE - COMPARISON WITH N-(TERT-BUTOXYCARBONYL)GLYCINE
    VANMEERVELT, L
    DEWAEL, K
    ZEEGERSHUYSKENS, T
    JOURNAL OF MOLECULAR STRUCTURE, 1995, 356 (03) : 183 - 190
  • [9] Synthesis of unusual amino acids:: N-(tert-butoxycarbonyl)-L-vinyl glycine and N-(tert-butoxycarbonyl)-L-homophenylalanine
    Chandrasekhar, S
    Raza, A
    Takhi, M
    TETRAHEDRON-ASYMMETRY, 2002, 13 (04) : 423 - 428
  • [10] SYNTHESIS OF PROTECTED INDOLES FROM N-(TERT-BUTOXYCARBONYL)-2-ALKYLANILINES
    CLARK, RD
    MUCHOWSKI, JM
    SOUCHET, M
    REPKE, DB
    SYNLETT, 1990, (04) : 207 - 208
12345