TBHP-promoted oxidative cyclization of o-alkynylquinoline aldehydes: Metal/additive-free domino synthesis of pyrano[4,3-b]quinolin-1-ones

被引：9
作者：
Singh, Jay Bahadur [1 ]
Mishra, Kalpana [1 ]
Gupta, Tanu [1 ]
Singh, Radhey M. [1 ]
机构：
[1] Banaras Hindu Univ, Inst Sci, Ctr Adv Study, Dept Chem, Varanasi, Uttar Pradesh, India
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 11期
关键词：
Metal free; Additive free; Radical reaction; TBHP; Pyrano[4,3-b]quinolin-1-ones; ONE-POT SYNTHESIS; C-H FUNCTIONALIZATION; TERT-BUTYL PERESTERS; ELECTROPHILIC CYCLIZATION; EFFICIENT SYNTHESIS; FACILE SYNTHESIS; INTRAMOLECULAR CARBONYLATION; PYRANOQUINOLINE ALKALOIDS; QUINOLINE ALKALOIDS; SELECTIVE SYNTHESIS;
D O I：
10.1016/j.tetlet.2018.01.083
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
TBHP-promoted domino synthesis of pyrano[4,3-b]quinolin-1-ones is described from o-alkynylquinoline aldehydes. The radical reaction proceeded without metal and additive via oxidation of aldehydic C-H bond into C-OH bond followed by intramolecular 6-endo-dig cyclization. The probable mechanism is discussed. (C) 2018 Published by Elsevier Ltd.
引用
收藏
页码：1019 / 1022
页数：4
相关论文
共 76 条
  • [11] NHC Catalyzed Oxidations of Aldehydes to Esters: Chemoselective Acylation of Alcohols in Presence of Amines
    De Sarkar, Suman
    Grimme, Stefan
    Studer, Armido
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) : 1190 - +
  • [12] Organocatalyzed Anodic Oxidation of Aldehydes
    Finney, Eric E.
    Ogawa, Kelli A.
    Boydston, Andrew J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) : 12374 - 12377
  • [13] The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations
    Girard, Simon A.
    Knauber, Thomas
    Li, Chao-Jun
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) : 74 - 100
  • [14] Silver versus gold catalysis in tandem reactions of carbonyl functions onto alkynes: A versatile access to furoquinoline and pyranoquinoline cores
    Godet, Thomas
    Vaxelaire, Carine
    Michel, Carine
    Milet, Anne
    Belmont, Philippe
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (19) : 5632 - 5641
  • [15] Biomimetic Carbene-Catalyzed Oxidations of Aldehydes Using TEMPO
    Guin, Joyram
    De Sarkar, Suman
    Grimme, Stefan
    Studer, Armido
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (45) : 8727 - 8730
  • [16] Temperature-controlled solvent-free selective synthesis of tert-butyl peresters or acids from benzyl cyanides in the presence of the TBHP/Cu(OAc)2 system
    Hashemi, H.
    Saberi, D.
    Poorsadeghi, S.
    Niknam, Kh.
    [J]. RSC ADVANCES, 2017, 7 (13): : 7619 - 7622
  • [17] A Regioselective Metal-Free Construction of 3-Aroyl Coumarins by Csp2-H Functionalization
    Jafarpour, Farnaz
    Abbasnia, Masoumeh
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (23) : 11982 - 11986
  • [18] Iron-catalyzed/mediated oxidative transformation of C-H bonds
    Jia, Fan
    Li, Zhiping
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (02): : 194 - 214
  • [19] Synthesis of novel pyrano[2,3-b]quinolines from simple acetanilides via intramolecular 1,3-dipolar cycloaddition
    Kalita, Pabitra K.
    Baruah, Biswajita
    Bhuyan, Pulak J.
    [J]. TETRAHEDRON LETTERS, 2006, 47 (44) : 7779 - 7782
  • [20] Nano CuO Catalyzed Cross Dehydrogenative Coupling (CDC) of Aldehydes to Anhydrides
    Khatun, Nilufa
    Santra, Sourav Kumar
    Banerjee, Arghya
    Patel, Bhisma K.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (06) : 1309 - 1313
12345678