N-Heterocyclization of Naphthylamines with 1,2-and 1,3-Diols Catalyzed by an Iridium Chloride/BINAP System

被引：76
作者：
Aramoto, Hiroomi
Obora, Yasushi
Ishii, Yasutaka [1 ]
机构：
[1] Kansai Univ, Fac Chem Mat & Bioengn, Dept Chem & Mat Engn, Osaka 5648680, Japan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 02期
关键词：
PRIMARY ALCOHOLS; KETONES; CYCLIZATION; QUINOLINES;
D O I：
10.1021/jo801966u
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Benzoquinoline derivatives were successfully synthesized by iridium-catalyzed N-heterocyclization of naphthylamines with diols. For instance, the reaction of 1-naphthylamine with 1,3-propanediol catalyzed by IrCl3 combined with BINAP as a ligand produced 7,8-benzoquinoline in quantitative yield. The N-heterocyclization reaction was found to be markedly influenced by the ligands employed. Benzoindoles were also synthesized by the same strategy from napthylamines with 1,2-diols. A reaction mechanism for the N-heterocyclization of naphthylamines with 1,3-diols by IrCl3 was proposed.
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收藏
页码：628 / 633
页数：6
相关论文
共 26 条
  • [1] Thermal cyclization of N-[2-(2-propenyl)-1-naphthyl] ketenimines:: intramolecular Diels-Alder reaction versus [1,5] hydrogen migration.: Synthesis of dibenz[b,h]acridines and benzo[h]quinolines
    Alajarín, M
    Vidal, A
    Ortín, MM
    [J]. TETRAHEDRON, 2005, 61 (32) : 7613 - 7621
  • [2] SYNTHESIS OF ALPHA-MONOSUBSTITUTED INDOLES
    AUGUSTINE, RL
    GUSTAVSE.AJ
    WANAT, SF
    PATTISON, IC
    HOUGHTON, KS
    KOLETAR, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (17) : 3004 - 3011
  • [3] THE REACTION OF VINYL GRIGNARD-REAGENTS WITH 2-SUBSTITUTED NITROARENES - A NEW APPROACH TO THE SYNTHESIS OF 7-SUBSTITUTED INDOLES
    BARTOLI, G
    PALMIERI, G
    BOSCO, M
    DALPOZZO, R
    [J]. TETRAHEDRON LETTERS, 1989, 30 (16) : 2129 - 2132
  • [4] N-ARYL-ETHENESULFENAMIDES - THERMAL TRANSFORMATION OF 2 N-(1-NAPHTHYL)-ETHENESULPHENAMIDES INTO 1H-BENZ[G]INDOLES
    BAUDIN, JB
    JULIA, SA
    RUEL, O
    [J]. TETRAHEDRON, 1987, 43 (05) : 881 - 889
  • [5] Palladium-catalyzed arylation of linear and cyclic polyamines
    Beletskaya, IP
    Bessmertnykh, AG
    Averin, AD
    Denat, F
    Guilard, R
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (02) : 261 - 280
  • [6] BRYANT S, 1991, J CHEM SOC, P93
  • [7] Ruthenium-catalysed synthesis of indoles from anilines and trialkanolamines in the presence of tin(II) chloride dihydrate
    Cho, CS
    Lim, HK
    Shim, SC
    Kim, TJ
    Choi, HJ
    [J]. CHEMICAL COMMUNICATIONS, 1998, (09) : 995 - 996
  • [8] Synthesis of isoindolinones via carbonylative cyclisation of 2-(2-bromophenyl)-2-oxazolines by a bimetallic palladium-nickel catalyst system
    Cho, CS
    Lee, JW
    Lee, DY
    Shim, SC
    Kim, TJ
    [J]. CHEMICAL COMMUNICATIONS, 1996, (18) : 2115 - 2116
  • [9] Synthesis, characterisation and antimicrobial activity of new benzo[a] phenoxazine based fluorophores
    Frade, Vania H. J.
    Sousa, Maria J.
    Moura, Joao C. V. P.
    Goncalves, M. Sameiro T.
    [J]. TETRAHEDRON LETTERS, 2007, 48 (47) : 8347 - 8352
  • [10] Functionalised benzo[a]phenoxazine dyes as long-wavelength fluorescent probes for amino acids
    Frade, Vania H. J.
    Coutinho, Paulo J. G.
    Moura, Joao C. V. P.
    Goncalves, M. Sameiro T.
    [J]. TETRAHEDRON, 2007, 63 (07) : 1654 - 1663
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