Synthesis of 3-aryl-3-benzazepines via aryne [1,2] Stevens rearrangement of 1,2,3,4-tetrahydroisoquinolines

被引：12
|
作者：
Pan, Xuan
Liu, Zhanzhu [1 ]
机构：
[1] Peking Union Med Coll, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 11期
关键词：
TERTIARY-AMINES; N-ARYLATION; POTENT; RECEPTOR; DISCOVERY; ANTAGONISTS; ACCESS; CO2;
D O I：
10.1039/c8qo00275d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method for the synthesis of 3-aryl-3-benzazepines via aryne induced [1,2] Stevens rearrangement of 1,2,3,4-tetrahydroisoquinolines is described. This approach provided straightforward access to 3-aryl-3-benzazepines in moderate to good yields under transition-metal-free and strong-base-free conditions. Temperature-dependent -arylated products of the carbonyl group were also obtained. Preliminary mechanistic studies suggest both 3-aryl-3-benzazepines and -arylated products of the carbonyl group were generated via the rearrangement of nitrogen ylide intermediates.
引用
收藏
页码：1798 / 1810
页数：13
相关论文
共 50 条
  • [31] STUDIES ON 1,2,3,4-TETRAHYDROISOQUINOLINES .2. A ONE-POT SYNTHESIS OF 1-ARYLMETHYL-1,2,3,4-TETRAHYDROISOQUINOLINES FROM AN ISOQUINOLINIUM SALT
    YAMADA, K
    ITOH, N
    IKEZAWA, K
    KIYOMOTO, A
    IWAKUMA, T
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1981, 29 (07) : 1848 - 1853
  • [32] Rapid Microwave-Assisted Synthesis of N-Aryl 1,2,3,4-Tetrahydroisoquinolines
    Forni, Jose Augusto
    Brzozowski, Martin
    Tsanaktsidis, John
    Savage, G. Paul
    Polyzos, Anastasios
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2015, 68 (12) : 1890 - 1893
  • [33] SYNTHESIS OF 8-ARYL-1,2,3,4-TETRAHYDROISOQUINOLINES AS DOPAMINE ANTAGONISTS
    ELLEFSON, CR
    PRODAN, KA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1979, (APR): : 11 - 11
  • [34] SUBSTITUTED 1-CYANO-1,2,3,4-TETRAHYDROISOQUINOLINES
    BOHME, H
    SCHWEITZ.R
    ARCHIV DER PHARMAZIE UND BERICHTE DER DEUTSCHEN PHARMAZEUTISCHEN GESSELSCHAFT, 1970, 303 (03): : 225 - &
  • [35] Synthesis of CF3-substituted 1,2,3,4-tetrahydroisoquinolines and 1,2,3,6-tetrahydropyridines
    I. Yu. Chernyshov
    V. V. Levin
    A. D. Dilman
    P. A. Belyakov
    M. I. Struchkova
    V. A. Tartakovsky
    Russian Chemical Bulletin, 2010, 59 : 2102 - 2107
  • [36] SYNTHESIS OF FUSED HETEROCYCLES - 1,2,3,4-TETRAHYDROISOQUINOLINES AND RING HOMOLOGS VIA SULFONAMIDOMETHYLATION
    ORAZI, OO
    CORRAL, RA
    GIACCIO, H
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (11): : 1977 - 1982
  • [37] SYNTHESIS OF ISOQUINOLINES .9. 1,2,3,4-TETRAHYDROISOQUINOLINES VIA MANNICH CONDENSATION
    BOBBITT, JM
    DUTTA, CP
    JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (06): : 2001 - &
  • [38] MONOPHENOLIC 1,2,3,4-TETRAHYDROISOQUINOLINES AND THEIR METHYL ETHERS
    SCHENKER, F
    SCHMIDT, RA
    WILLIAMS, T
    BROSSI, A
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1971, 8 (04) : 665 - &
  • [39] Synthesis of CF3-substituted 1,2,3,4-tetrahydroisoquinolines and 1,2,3,6-tetrahydropyridines
    Chernyshov, I. Yu.
    Levin, V. V.
    Dilman, A. D.
    Belyakov, P. A.
    Struchkova, M. I.
    Tartakovsky, V. A.
    RUSSIAN CHEMICAL BULLETIN, 2010, 59 (11) : 2102 - 2107
  • [40] SYNTHESIS OF 1,2,3,4-TETRAHYDROISOQUINOLINES FROM ALPHA-METHYLDOPA
    RACHLIN, S
    WORNING, K
    ENEMARK, J
    TETRAHEDRON LETTERS, 1968, (39) : 4163 - &
12345