Heterocyclization of 1- and 2-alkynyl-9,10-anthraquinones: new synthetic and mechanistic aspects

被引：3
作者：
Vasilevskiy, S. F. [1 ]
Baranov, D. S. [1 ]
机构：
[1] Russian Acad Sci, Voevodsky Inst Chem Kinet & Combust, Siberian Branch, Novosibirsk 610090, Russia
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2013年 / 49卷 / 01期
基金：
俄罗斯基础研究基金会;
关键词：
alkynes; 9,10-anthraquinone; nitrogen heterocycles; cyclization; mechanisms; reactivity; rearrangements; ACETYLENIC DERIVATIVES; RING-CLOSURE; CHEMISTRY; ALKALOIDS; CYCLIZATIONS; CYANOPHENOLS; GUANIDINE; QUINONES; REVERSAL; CASCADE;
D O I：
10.1007/s10593-013-1235-z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New data (2005-2012) on the peculiarities and common characteristics of cascade reactions of 1- and 2-alkynyl-9,10-anthraquinones with polyfunctional reagents (guanidine, urea, thiourea) and also intramolecular heterocyclizations of ortho-amino derivatives of 1- and 2-alkynyl-9,10-anthraquinones are reviewed. Mechanisms for new reactions are suggested.
引用
收藏
页码：140 / 151
页数：12
相关论文
共 32 条
  • [1] [Anonymous], 2008, ZH ORG KHIM
  • [2] RULES FOR RING-CLOSURE
    BALDWIN, JE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) : 734 - 736
  • [3] Baranov D. S., 2010, IZV AKAD NAUK K, P1008
  • [4] Baranov D. S., 2010, THESIS NOVOSIBIRSK
  • [5] Baranov D. S., 2012, IZV AKAD NAUK K, P1554
  • [6] Synthesis of 2-amino-5,5-dialkyl-4-arylmethylidene-2-oxazolines from 2-alkyl-4-arylbut-3-yn-2-ols and guanidine
    Baranov, Denis S.
    Ryabichev, Aleksey A.
    Mamatyuk, Victor I.
    Gatilov, Yurii V.
    Kartsev, Victor G.
    Vasilevsky, Sergei F.
    [J]. MENDELEEV COMMUNICATIONS, 2012, 22 (02) : 114 - 116
  • [7] Urea as an organic solvent and reagent for the addition/cyclization/fragmentation cascades leading to 2-R-7H-dibenzo[de,h]quinolin-7-one analogues of Aporphinoid alkaloids
    Baranov, Denis S.
    Vasilevsky, Sergei F.
    Gold, Brian
    Alabugin, Igor V.
    [J]. RSC ADVANCES, 2011, 1 (09) : 1745 - 1750
  • [8] Multichannel reaction of 1-(3′-hydroxy-3′-methylbutynyl)-9,10-anthraquinone with guanidine
    Baranov, Denis S.
    Vasilevsky, Sergei F.
    Mamatyuk, Victor I.
    Gatilov, Yurii V.
    [J]. MENDELEEV COMMUNICATIONS, 2009, 19 (06) : 326 - 328
  • [9] The sonogashira reaction:: A booming methodology in synthetic organic chemistry
    Chinchilla, Rafael
    Najera, Carmen
    [J]. CHEMICAL REVIEWS, 2007, 107 (03) : 874 - 922
  • [10] Dembitsky VM, 2006, NAT PROD COMMUN, V1, P405
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