A New [2+2+1] Heterocyclization for the Synthesis of 2,3,5-Trisubstituted Thiophenes under Microwave Irradiation

被引：5
|
作者：
Xu, Hai-Wei
Ma, Guan-Hua
Jiang, Bo [1 ]
Tu, Shu-Jiang
机构：
[1] Jiangsu Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Jiangsu, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2013年 / 45卷 / 24期
基金：
美国国家科学基金会;
关键词：
heterocyclization; substituted thiophene; three-component reactions; -thiocyanato ketone; 3-(2-aryl-2-oxoethylidene)-2-oxindole; SUBSTITUTED THIOPHENES; MOLECULAR DESIGN;
D O I：
10.1055/s-0033-1339917
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new three-component strategy for the efficient synthesis of 2,3,5-trisubstituted thiophene derivatives through a [2+2+1] heterocyclization between 3-(2-aryl-2-oxoethylidene)-2-oxindoles and -thiocyanato ketones under microwave irradiation is described. The bond-forming efficiency, accessibility, and generality of this synthesis make it highly valuable to assemble thiophene scaffolds.
引用
收藏
页码：3392 / 3398
页数：7
相关论文
共 50 条
  • [21] Synthesis of New 2-(Oxiran-2-yl)-1,3-oxazoles
    O. V. Shablykin
    M. A. Volosheniuk
    V. S. Brovarets
    Russian Journal of General Chemistry, 2018, 88 : 1542 - 1545
  • [22] HETEROCYCLIZATION OF 3-PROPARGYLSULFANYL-5 PHENYL-1,2,4-TRIAZINE: TANDEM REACTIONS WITH BROMINE LEADING TO NEW DERIVATIVES OF 7 PHENYL[1,3]THIAZOLO[3,2-B][1,2,4]TRIAZINIUM
    Rybakova, A. V.
    Kim, D. G.
    Danilina, E. I.
    Sazhaeva, O. V.
    Ezhikova, M. A.
    Kodess, M. I.
    IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA I KHIMICHESKAYA TEKHNOLOGIYA, 2020, 63 (06): : 19 - 24
  • [23] Synthesis of New 2-(Oxiran-2-yl)-1,3-oxazoles
    Shablykin, O. V.
    Volosheniuk, M. A.
    Brovarets, V. S.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2018, 88 (07) : 1542 - 1545
  • [24] Cascade Regioselective Heterocyclization of 2-Acyl-1,1,3,3-tetracyanopropenides: Synthesis of Pyrrolo[3,4-c]pyridine and Pyrrolo[3,4-d]thieno[2,3-b]pyridine Derivatives
    Grigor'ev, Arthur A.
    Karpov, Sergey V.
    Kayukov, Yakov S.
    Gracheva, Iuliia A.
    Tafeenko, Victor A.
    SYNLETT, 2017, 28 (13) : 1592 - 1595
  • [25] One-pot synthesis of 2,1-benzisoxazoles (anthranils) by a stannous chloride-mediated tandem reduction-heterocyclization of 2-nitroacylbenzenes under neutral conditions
    Chauhan, Jay
    Fletcher, Steven
    TETRAHEDRON LETTERS, 2012, 53 (37) : 4951 - 4954
  • [26] Heterocyclization of 3-aminocamphor and 3-aminoisoborneol derivatives with cyclic β-diketones and formaldehyde. Synthesis of optically active 1,2,3,4-tetrahydroquinoline derivatives with terpene substituents
    A. P. Kadutskii
    N. G. Kozlov
    L. L. Frolova
    I. N. Alekseev
    A. V. Kuchin
    Chemistry of Natural Compounds, 2012, 48 : 404 - 411
  • [27] Heterocyclization of 3-aminocamphor and 3-aminoisoborneol derivatives with cyclic β-diketones and formaldehyde. Synthesis of optically active 1,2,3,4-tetrahydroquinoline derivatives with terpene substituents
    Kadutskii, A. P.
    Kozlov, N. G.
    Frolova, L. L.
    Alekseev, I. N.
    Kuchin, A. V.
    CHEMISTRY OF NATURAL COMPOUNDS, 2012, 48 (03) : 404 - 411
  • [28] Two routes of heterocyclization of 2-alkynylanthraquinone-1-diazonium salts.: The synthesis of 1H-naphtho[2,3-h]cinnoline-4,7,12-trione
    Fedenok, LG
    Barabanov, II
    Ivanchikova, ID
    TETRAHEDRON, 2001, 57 (07) : 1331 - 1334
  • [29] Improved approaches in the synthesis of new 2-(1,3-thiazolidin-2Z-ylidene)acetophenones
    Ortega-Alfaro, MC
    López-Cortés, JG
    Sánchez, HR
    Toscano, RA
    Carrillo, GP
    Alvarez-Toledano, C
    ARKIVOC, 2005, : 356 - 365
  • [30] N-iodosuccinimide:: An efficient reagent for regioselective heterocyclization of 3-allyl-4-hydroxy[1]benzopyran-2-ones
    Majumdar, KC
    Basu, PK
    Roy, B
    SYNTHETIC COMMUNICATIONS, 2003, 33 (20) : 3621 - 3630
12345