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
  • [31] (-)-N-(tert-butoxycarbonyl)-L-proline-2-thioamide (boc-L-pro-thioamide)
    Oku, Hiroyuki
    Yoshinari, Takamasa
    Yamada, Keiichi
    Katakai, Ryoichi
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O5298 - O5300
  • [32] Dicyclohexylaminium N-(tert-butoxycarbonyl)-L-threoninate:: a monoclinic structure with Z′=4
    Bryndal, Iwona
    Lis, Tadeusz
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : o1444 - o1447
  • [33] Directed lithiation of N-(tert-butoxycarbonyl)aminoisoxazole: Synthesis of 4-substituted aminoisoxazoles
    Konoike, T
    Kanda, Y
    Araki, Y
    TETRAHEDRON LETTERS, 1996, 37 (19) : 3339 - 3342
  • [34] THE CRYSTAL-STRUCTURE OF N-(TERT-BUTOXYCARBONYL)-L-METHIONYLGLYCINE BENZYL ESTER
    YAMANE, T
    UMEMURA, T
    KOJIMA, T
    YAMADA, Y
    ASHIDA, T
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (04) : 908 - 912
  • [35] A new facile method for the chemoselective reductive transformation of azides to N-(tert-butoxycarbonyl) amines
    Kotsuki, H
    Ohishi, T
    Araki, T
    TETRAHEDRON LETTERS, 1997, 38 (12) : 2129 - 2132
  • [36] Directed lithiation of N-(tert-butoxycarbonyl)aminoisoxazole: synthesis of 4-substituted aminoisoxazoles
    Tetrahedron Lett, 19 (3339):
  • [37] Chemical and enzymatic resolution of (R,S)-N-(tert-butoxycarbonyl)-3-hydroxymethylpiperidine
    Goswami, A
    Howell, JM
    Hua, EY
    Mirfakhrae, KD
    Soumeillant, MC
    Swaminathan, S
    Qian, XH
    Quiroz, FA
    Vu, TC
    Wang, XB
    Zheng, B
    Kronenthal, DR
    Patel, RN
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (04) : 415 - 420
  • [38] NUCLEOSIDE ANNELATING REAGENTS - N-(TERT-BUTOXYCARBONYL)-2-BROMOACETAMIDE AND 2-CHLOROKETENE DIETHYL ACETAL
    LEONARD, NJ
    CRUICKSHANK, KA
    JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (14): : 2480 - 2488
  • [39] SIMPLE METHOD OF PREPARATION OF TERT-BUTOXYCARBONYL AMINO-ACIDS
    GRZONKA, Z
    LAMMEK, B
    SYNTHESIS-STUTTGART, 1974, (09): : 661 - 662
  • [40] ONE-POT TRANSFORMATION OF AZIDO-GROUP TO N-(TERT-BUTOXYCARBONYL)AMINO GROUP
    SAITO, S
    NAKAJIMA, H
    INABA, M
    MORIWAKE, T
    TETRAHEDRON LETTERS, 1989, 30 (07) : 837 - 838
12345