Efficient synthesis of new 1-alkyl(aryl)-5-(3,3,3-trihalo-2-oxopropylidene)-1H-pyrrol-2(5H)-ones

被引：7
|
作者：
Flores, Alex F. C. [1 ]
Pizzuti, Lucas [2 ]
Piovesan, Luciana A. [3 ]
Flores, Darlene C. [1 ]
Malavolta, Juliana L. [1 ]
Pereira, Claudio M. P. [4 ]
机构：
[1] Univ Fed Santa Maria, Dept Quim, NUQUIMHE, BR-97105900 Santa Maria, RS, Brazil
[2] Fundacao Univ Fed Grande Dourados, BR-79804970 Dourados, MS, Brazil
[3] Univ Fed Rio de Janeiro, Fac Farm, Lab Avaliacao & Sintese Subst Bioat, LASSBio, BR-21941590 Rio De Janeiro, Brazil
[4] Univ Fed Pelotas, Inst Quim & Geociencias, BR-96010900 Pelotas, RS, Brazil
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 37期
关键词：
LACTONES;
D O I：
10.1016/j.tetlet.2010.07.073
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of 1-alkyl(aryl)-5-(3,3,3-trihalo-2-oxopropylidene)-1H-pyrrol-2(5H)-ones 5, 6a-d from 1-alkyl(aryl)-4-bromo-5-(3,3,3-trihalo-2-oxopropylidene)-1H-pyrrolidin-2-ones 3, 4a-d is reported. The 1-alkyl(aryl)-4-bromo-5-(3,3,3-trihalo-2-oxopropylidene)-1H-pyrrolidin-2-ones 3, 4a-d were obtained from regiospecific bromination of 1-alkyl(aryl)-5-(3,3,3-trihalo-2-oxopropylidene)-1H-pyrrolidin-2-ones 1, 2a-d with molecular bromine. The NMR and X-ray diffraction data showed that 1-alkyl(aryl)-5-(3,3,3-trihalo-2-oxopropylidene)-1H-pyrrolidin-2-ones were brominated at 4-position in the pyrrolidin-2-one ring. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4908 / 4910
页数：3
相关论文
共 50 条
  • [21] Direct Synthesis of 4-Acetyl-1-alkyl-1H-pyrrol-2(5H)-ones from Difunctionalized Allyl Bromide
    Jebali, Khaoula
    Arfaoui, Aicha
    Saadi, Fatma
    Lebreton, Jacques
    Amri, Hassen
    SYNTHETIC COMMUNICATIONS, 2014, 44 (23) : 3400 - 3407
  • [22] A NEW FACILE SYNTHESIS OF 5-ALKYL-2-ARYL-3H-PYRAZOL-3-ONES
    CHEN, BC
    HUANG, X
    MA, SM
    SYNTHETIC COMMUNICATIONS, 1987, 17 (12) : 1519 - 1522
  • [23] AN EFFICIENT SYNTHESIS OF 3-ALKYL-5-ARYL-2(1H)-PYRAZINONES
    BRADBURY, RH
    GRIFFITHS, D
    RIVETT, JE
    HETEROCYCLES, 1990, 31 (09) : 1647 - 1653
  • [24] Synthesis and Biological Activity of 4-Amino-1,3,5-triaryl-1H-pyrrol-2(5H)-ones
    Aleksanyan, M. V.
    Harutyunyan, G. K.
    Stepanyan, H. M.
    Muradyan, R. Y.
    Gasparyan, S. P.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 60 (12) : 2393 - 2400
  • [25] Azo coupling of 5-substituted furan-2(3H)-ones and 1H-pyrrol-2(3H)-ones with arene(hetarene)diazonium salts
    Gavkus, D. N.
    Maiorova, O. A.
    Borisov, M. Yu
    Egorova, A. Yu
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 48 (09) : 1229 - 1232
  • [26] Synthesis of 5-[1-Aryl-pyrrol-2-yl]-1H-tetrazole
    Liu, Wei
    Ma, Yuan
    Yin, Ying-Wu
    Zhao, Yu-Fen
    Gaodeng Xuexiao Huaxue Xuebao/Chemical Journal of Chinese Universities, 2006, 27 (08): : 1472 - 1475
  • [27] Synthesis of arylidene derivatives of 1-aryl-3H-pyrrol-2-ones
    Egorova A.Yu.
    Nesterova V.V.
    Chemistry of Heterocyclic Compounds, 2004, 40 (08) : 1002 - 1006
  • [28] Synthesis of 5-[1-aryl-pyrrol-2-yl]-1H-tetrazole
    Liu Wei
    Ma Yuan
    Yin Ying-Wu
    Zhao Yu-Fen
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2006, 27 (08): : 1472 - 1475
  • [29] Ugi reaction-derived 1H-pyrrol-2(5H)-ones proved as valid precursors to a new class of heterocyclic α-diazocarbonyl compounds
    Budeev, Anton
    Kantin, Grigory
    Dar'in, Dmitry
    Krasavin, Mikhail
    TETRAHEDRON LETTERS, 2022, 89
  • [30] Triethylammonium hydrogen sulfate as a catalyst for the preparation of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-one derivatives
    Shafiee, Mohammad Reza Mohammad
    Najafabadi, Batool Hojati
    Ghashang, Majid
    JOURNAL OF CHEMICAL RESEARCH, 2011, (11) : 634 - 636
12345