Synthesis of Benzoxazoles by an Efficient Ullmann-Type Intramolecular C(aryl)-O Bond-Forming Coupling Cyclization with a BINAM-Copper(II) Catalyst

被引：36
作者：
Naidu, Ajay B. [1 ]
Sekar, Govindasamy [1 ]
机构：
[1] Indian Inst Technol Madras, Dept Chem, Madras 600036, Tamil Nadu, India
来源：
SYNTHESIS-STUTTGART | 2010年 / 04期
关键词：
copper catalyst; nitrogen ligands; C-O bond formation; Ullmann coupling; benzoxazole synthesis; REVERSE-TRANSCRIPTASE INHIBITORS; BUTYL HYDROPEROXIDE; PARALLEL SYNTHESIS; CARBOXYLIC-ACIDS; CARBONYL OXYGEN; MILD CONDITIONS; O-ARYLATION; DERIVATIVES; OXIDATION; DESIGN;
D O I：
10.1055/s-0029-1218589
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A wide range of 2-substituted benzoxazoles were synthesized from the corresponding N-(2-iodophenyl) benzamides through intramolecular C-(aryl)-O bond formation via Ullmann-type coupling cyclization in the presence of a catalytic amount of an easily available BINAM-copper(II) complex under very mild reaction conditions (82 degrees C). Less reactive bromo and chloro analogues of the N-(2-halophenyl) benzamides were also successfully cyclized to produce benzoxazoles, without increasing the catalyst loading.
引用
收藏
页码：579 / 586
页数：8
相关论文
共 56 条
  • [1] Palladium-Catalyzed Direct Arylations of Heteroarenes with Tosylates and Mesylates
    Ackermann, Lutz
    Althammer, Andreas
    Fenner, Sabine
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) : 201 - 204
  • [2] QUINONE IMIDES .25. ORTHO-QUINONEDIBENZIMIDES
    ADAMS, R
    WAY, JW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (10) : 2763 - 2769
  • [3] Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648)
    Aiello, Stefania
    Wells, Geoffrey
    Stone, Erica L.
    Kadri, Hachemi
    Bazzi, Rana
    Bell, David R.
    Stevens, Malcolm F. G.
    Matthews, Charles S.
    Bradshaw, Tracey D.
    Westwell, Andrew D.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (16) : 5135 - 5139
  • [4] A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary amides into benzoxazoles
    Altenhoff, G
    Glorius, F
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) : 1661 - 1664
  • [5] Copper-catalysed intramolecular O-arylation of aryl chlorides and bromides:: a straightforward approach to benzo[d]oxazoles in water
    Barbero, Nekane
    Carril, Monica
    SanMartin, Raul
    Dominguez, Esther
    [J]. TETRAHEDRON, 2007, 63 (42) : 10425 - 10432
  • [6] Iron-catalyzed intramolecular O-arylation:: Synthesis of 2-aryl benzoxazoles
    Bonnamour, Julien
    Bolm, Carsten
    [J]. ORGANIC LETTERS, 2008, 10 (13) : 2665 - 2667
  • [7] Bourgrin K., 1998, TETRAHEDRON, V54, P8055
  • [8] Brière JF, 2000, HETEROCYCLES, V52, P1371
  • [9] Synthesis, structure-activity relationships, and antitumor studies of 2-benzoxazolyl hydrazones derived from alpha-(N)-acyl heteroaromatics
    Easmon, Johnny
    Purstinger, Gerhard
    Thies, Katrin-Sofia
    Heinisch, Gottfried
    Hofmann, Johann
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (21) : 6343 - 6350
  • [10] INVESTIGATION OF THE SYNTHESIS OF BENZOXAZOLE VIA ARYNE REACTION
    ELSHEIKH, MI
    MARKS, A
    BIEHL, ER
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (16) : 3256 - 3259
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