A Novel Synthesis of N-Unsubstituted β-Enamino Thioesters from 3-Arylisoxazoles and 3-Aryl-5-phenylthio-2-isoxazolines

被引：12
|
作者：
Vitale, Paola [1 ]
Di Nunno, Leonardo [1 ]
Scilimati, Antonio [1 ]
机构：
[1] Univ Bari A Moro, Dipartimento Farmacochim, I-70125 Bari, Italy
来源：
SYNTHESIS-STUTTGART | 2010年 / 18期
关键词：
cycloaddition; lithiation; nucleophilic addition; 3-arylisoxazoles; beta-enaminoacyl derivatives; ASYMMETRIC HYDROGENATION; EFFICIENT SYNTHESIS; CARBONYL-COMPOUNDS; ACID-DERIVATIVES; ISOXAZOLES; 5-HYDROXY-2-ISOXAZOLINES; 2-ISOXAZOLINES; FRAGMENTATION; DIMERIZATION; REACTIVITY;
D O I：
10.1055/s-0030-1258186
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel procedure for the synthesis of N-unsubstituted beta-enamino thioesters, (Z)-S-phenyl 3-amino-3-arylprop-2-enethioates, from 3-arylisoxazoles or 3-aryl-5-phenylthio-2-isoxazolines is described and a plausible mechanism for the reaction is proposed. Some examples of conversion of one b-enamino thioester [(Z)-S-phenyl 3-amino-3-phenylprop-2-enethioate] into N-unsubstituted beta-enaminoacyl derivatives (beta-enamino esters, beta-enamino amides, and beta-keto amides) are also reported.
引用
收藏
页码：3195 / 3203
页数：9
相关论文
共 50 条
  • [31] 3-Aryl-5-vinyl-2-isoxazolines and 3-aryl-5-vinylisoxazoles from aryl nitrile oxides and methyl vinyl ketone lithium enolate: Reaction limits and synthetic utility exploitation
    Salomone, Antonio
    Scilimati, Antonio
    Vitale, Paola
    Synthesis (Germany), 2015, 47 (06) : 807 - 816
  • [32] Two approaches toward the regio- and stereoselective synthesis of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro-[chromeno[3,4-c]pyrrolidine-1,3′-oxindoles]
    Korotaev, Vladislav Yu
    Barkovskii, Savelii, V
    Kutyashev, Igor B.
    Ulitko, Maria, V
    Barkov, Alexey Yu
    Zimnitskiy, Nikolay S.
    Kochnev, Ivan A.
    Sosnovskikh, Vyacheslav Ya
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (06) : 679 - 690
  • [33] A FACILE SYNTHESIS OF 5(3)-ARYL-3(5)-CYANOMETHYLPYRAZOLES FROM 6-ARYL-3-CYANO-4-METHYLTHIOPYRAN-2-ONES
    RAM, VJ
    VERMA, M
    HUSSAINI, FA
    SHOEB, A
    JOURNAL OF CHEMICAL RESEARCH-S, 1991, (04): : 98 - 99
  • [34] A simple and convenient synthesis of 4-methyl-3-nitro-2-trihalomethyl-2H-chromenes from N-unsubstituted imines of 2-hydroxyacetophenones and trichloro(trifluoro)ethylidene nitromethanes
    Korotaev, Vladislav Yu.
    Sosnovskikh, Vyacheslav Ya.
    Kutyashev, Igor B.
    Barkov, Alexey Yu.
    Matochkina, Evgeniya G.
    Kodess, Mikhail I.
    TETRAHEDRON, 2008, 64 (22) : 5055 - 5060
  • [35] AN EFFICIENT, REGIOCONTROLLED SYNTHESIS OF 5-ARYL-2-CARBETHOXYPYRROLES FROM 3-ARYL-3-CHLOROPROPENIMINIUM SALTS
    GUPTON, JT
    KROLIKOWSKI, DA
    YU, RH
    VU, P
    SIKORSKI, JA
    DAHL, ML
    JONES, CR
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (20): : 5480 - 5483
  • [36] 3-Nitro-2H-chromenes in [3+2] cycloaddition reaction with azomethine ylides derived from N-unsubstituted α-amino acids and isatins: regio- and stereoselective synthesis of spirochromeno[3,4-c]pyrrolidines
    Igor B. Kutyashev
    Alexey Yu. Barkov
    Vladislav Yu. Korotaev
    Vyacheslav Ya. Sosnovskikh
    Chemistry of Heterocyclic Compounds, 2019, 55 : 529 - 540
  • [37] 3-Nitro-2H-chromenes in [3+2] cycloaddition reaction with azomethine ylides derived from N-unsubstituted α-amino acids and isatins: regio- and stereoselective synthesis of spirochromeno[3,4-c]pyrrolidines
    Kutyashev, Igor B.
    Barkov, Alexey Yu.
    Korotaev, Vladislav Yu.
    Sosnovskikh, Vyacheslav Ya.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (06) : 529 - 540
  • [38] Synthesis of N-Unsubstituted and N3-Substituted Quinazoline2,4(1H,3H)-diones from o-Aminobenzamides and CO2 at Atmospheric Pressure and Room Temperature
    Zhang, Lin
    Chen, Qian
    Li, Linlin
    Ma, Nana
    Tian, Jie
    Sun, Hao
    Xu, Qian
    Yang, Yuanyong
    Li, Chun
    ORGANIC LETTERS, 2023, 25 (14) : 2471 - 2475
  • [39] Ultrasound Assisted One-Pot Synthesis of Novel 3-(Aryl)-5-((4-(phenyldiazenyl)phenoxy)methyl)isoxazolines in Water
    El Mahmoudi, Ayoub
    Karrouchi, Khalid
    Tachallait, Hamza
    Bougrin, Khalid
    MOLBANK, 2022, 2022 (04)
  • [40] Synthesis of Novel 3-Aryl-5-dichloromethyl-Δ2-1,2,4-oxadiazolines
    Guirado, Antonio
    Sandoval, Jose A.
    Alarcon, Enrique
    Vera, Maria
    Bautista, Delia
    Galvez, Jesus
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (06) : 1873 - 1878
12345