Synthesis of substituted indenones and indanones by a Suzuki-Miyaura coupling/acid-promoted cyclisation sequence

被引：22
作者：
Butkevich, Alexey N. [1 ]
Ranieri, Beatrice [1 ]
Meerpoel, Lieven [2 ]
Stansfield, Ian [3 ]
Angibaud, Patrick [3 ]
Corbu, Andrei [1 ]
Cossy, Janine [1 ]
机构：
[1] ESPCI ParisTech, Chim Organ Lab, CNRS, F-75231 Paris 05, France
[2] Janssen Res & Dev, B-2340 Beerse, Belgium
[3] Janssen Res & Dev, Oncol & Med Chem, F-27106 Val De Reuil, France
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 05期
关键词：
FRIEDEL-CRAFTS REACTION; ONE-POT SYNTHESIS; C-H; CATALYZED ANNULATION; EFFICIENT SYNTHESIS; INTERNAL ALKYNES; ALLYLIC ALCOHOLS; VIROLA-SEBIFERA; 1-INDANONES; ACIDS;
D O I：
10.1039/c3ob41974f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A one-pot Suzuki-Miyaura cross-coupling/acid-catalyzed cyclisation leading to indenones and indanones in modest to good yields is reported.
引用
收藏
页码：728 / 731
页数：4
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共 32 条
  • [1] Tandem Suzuki-Miyaura Coupling/Acid-Catalyzed Cyclization between Vinyl Ether Boronates and Vinyl Halides: A Concise Approach to Polysubstituted Furans
    Butkevich, Alexey N.
    Meerpoel, Lieven
    Stansfield, Ian
    Angibaud, Patrick
    Corbu, Andrei
    Cossy, Janine
    [J]. ORGANIC LETTERS, 2013, 15 (15) : 3840 - 3843
  • [2] Two-Step One-Pot Synthesis of Benzoannulated Spiroacetals by Suzuki-Miyaura Coupling/Acid-Catalyzed Spiroacetalization
    Butkevich, Alexey N.
    Corbu, Andrei
    Meerpoel, Lieven
    Stansfield, Ian
    Angibaud, Patrick
    Bonnet, Pascal
    Cossy, Janine
    [J]. ORGANIC LETTERS, 2012, 14 (19) : 4998 - 5001
  • [3] A facile approach to the construction of 1H-Inden-1-one
    Chen, B
    Xie, XG
    Lu, JP
    Wang, QL
    Zhang, JY
    Tang, SC
    She, XG
    Pan, XF
    [J]. SYNLETT, 2006, (02) : 259 - 262
  • [4] Synthesis of 1-indanones by intramolecular Friedel-Crafts reaction of 3-arylpropionic acids catalyzed by Tb(OTf)3
    Cui, DM
    Zhang, C
    Kawamura, M
    Shimada, S
    [J]. TETRAHEDRON LETTERS, 2004, 45 (08) : 1741 - 1745
  • [5] Meldrum's acids as acylating agents in the catalytic intramolecular Friedel-Crafts reaction
    Fillion, E
    Fishlock, D
    Wilsily, A
    Goll, JM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (04) : 1316 - 1327
  • [6] AN EFFICIENT SYNTHESIS OF SELECTED INDENONES
    FLOYD, MB
    ALLEN, GR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (08) : 2647 - &
  • [7] Cobalt-catalyzed arylation of aldimines via directed C-H bond functionalization: addition of 2-arylpyridines and self-coupling of aromatic aldimines
    Gao, Ke
    Yoshikai, Naohiko
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (36) : 4305 - 4307
  • [8] Synthesis of indenols and indanones via catalytic cyclic vinylpalladation of aromatic aldehydes
    Gevorgyan, V
    Quan, LG
    Yamamoto, Y
    [J]. TETRAHEDRON LETTERS, 1999, 40 (21) : 4089 - 4092
  • [9] Rh(I)-catalyzed carbonylative cyclization reactions of alkynes with 2-bromophenylboronic acids leading to indenones
    Harada, Yasuyuki
    Nakanishi, Jun
    Fujihara, Hirokazu
    Tobisu, Mamoru
    Fukumoto, Yoshiya
    Chatani, Naoto
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) : 5766 - 5771
  • [10] On the identity of a neo-lignan from the fruits of Virola sebifera
    Harrowven, DC
    Newman, NA
    Knight, CA
    [J]. TETRAHEDRON LETTERS, 1998, 39 (37) : 6757 - 6760
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