Nucleophilic sulfanylation of 1,5-disubstituted pent-2-en-4-yn-1-ones

被引：20
作者：
Golovanov, A. A. [1 ]
Gusev, D. M. [1 ]
Vologzhanina, A. V. [2 ]
Bekin, V. V. [1 ]
Pisareva, V. S. [1 ]
机构：
[1] Togliatti State Univ, Tolyatti 445667, Russia
[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 50卷 / 01期
关键词：
MICHAEL ADDITION; THIOLS; KETONES;
D O I：
10.1134/S1070428014010035
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Regioselectivity of nucleophilic addition of benzenethiols and phenylmethanethiol to 1,5-diarylpent-2-en-4-yn-1-ones in ethanol in the presence of triethylamine at 0-30A degrees C is determined by the nucleophile nature. Phenylmethanethiol adds to the double bond, whereas benzenethiols add to the triple bond. The addition products, 1,5-diaryl-3-benzylsulfanylpent-4-yn-1-ones and 1,5-diaryl-5-(4-arylsulfanyl)penta-2,4-dien-1-ones, respectively, were isolated in 43-89% yield. Substituents in the aryl rings of the substrates did not affect the reaction direction.
引用
收藏
页码：13 / 20
页数：8
相关论文
共 50 条
  • [31] First Report of the Isolation of Novel Oxiranes in the I(III) Mediated Oxidation of 1-(4-Nitrophenyl)-3-arylprop-2-en-1-ones
    Prakash, Om
    Moriarty, Robert M.
    Chaudhri, Vishwas
    Pannu, Kamaljeet
    Pundeer, Rashmi
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 27 (04) : 327 - 328
  • [32] One-Pot, Three Component Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles Catalyzed by Heteropolyacid
    Heravi, Majid M.
    Zadsirjan, Vahideh
    Bakhtiari, Khadijeh
    Bamoharram, Fatemeh F.
    SYNTHESIS AND REACTIVITY IN INORGANIC METAL-ORGANIC AND NANO-METAL CHEMISTRY, 2013, 43 (03) : 259 - 263
  • [33] Synthesis of 3,5-Disubstituted Cyclohex-2-en-1-one via a Five-Step Domino Reaction Catalyzed by Secondary Amines: Formation of (E)-α,β-Unsaturated Methyl Ketones
    Ghorai, Manas K.
    Samanta, Sauvik
    Das, Subhomoy
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (12) : 1026 - 1030
  • [34] Regioselective Synthesis of Novel [1,2,4]Triazolo[1,5-a]pyridine Derivatives
    Ben Hassen, Manel
    Masmoudi, Fatma
    Zribi, Lazhar
    Trigui, Mohamed
    Ismaili, Lhassane
    Marco-Contelles, Jose
    Chabchoub, Fakher
    CHEMISTRYSELECT, 2021, 6 (05): : 945 - 950
  • [35] Base-Catalyzed Synthesis of Flavones via Thiol-Assisted Sequential Demethylation/Cyclization of 1-(2-Methoxyphenyl)prop-2-yn-1-ones
    Heck, Ritiele
    Anjos, Thiago
    Giehl, Maira R.
    Schumacher, Ricardo F.
    Godoi, Benhur
    SYNTHESIS-STUTTGART, 2022, 54 (20): : 4601 - 4607
  • [36] Functionalization of the "Bay Region" of Perylene in Reaction with 1-Arylalk-2-yn-1-ones Catalyzed by Trifluoromethanesulfonic Acid: One-Step Approach to 1-Acyl-2-alkylbenzo[ghi]perylenes
    Glodek, Marta
    Makal, Anna
    Plazuk, Damian
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (22) : 14165 - 14174
  • [37] Synthesis of α-2-deoxy-ulosides by Michael addition of hex-1-en-3-ones
    Lin, Zi-Ping
    Wong, Fung Fuh
    Chen, Yen-Bo
    Lin, Yu-Cheng
    Kimura, Masayuki
    Kaneko, Kimiyoshi
    Takayama, Hiroyuki
    Wu, Jin Bin
    Lin, Chun-Hung
    Lin, Hui-Chang
    TETRAHEDRON, 2013, 69 (11) : 2494 - 2500
  • [38] Enantioselective Synthesis of 4-Substituted 4,5-Dihydro-1H-[1,5]benzodiazepin-2(3H)-ones by the Lewis Base-Catalyzed Hydrosilylation
    Chen, Xing
    Zheng, Yongsheng
    Shu, Chang
    Yuan, Weicheng
    Liu, Bo
    Zhang, Xiaomei
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (21) : 9109 - 9115
  • [39] Chemoselective Synthesis of 1-Substituted 4-Amino-2-(trifluoromethyl)-1H-pyrroles through the Heterocyclization Reaction of 4-Methoxy-5-bromo-1,1,1-trifluoropent-3-en-2-ones with Amines
    Aquino, Estefania da C.
    Leonel, Guilherme
    Gariboti, Vanessa C.
    Frizzo, Clarissa P.
    Martins, Marcos A. P.
    Bonacorso, Helio G.
    Zanatta, Nilo
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24) : 12453 - 12459
  • [40] Opening of the pyridine ring in the system 1,1,1-trifluoro-4-phenylbut-3-yn-2-one-water. Stereoselective synthesis of 5-{[(1Z)-4,4,4-trifluoro-3-oxo-1-phenylbut-1-en-1-yl]amino}penta-2,4-dienal
    Andriyankova, L. V.
    Nikitina, L. P.
    Belyaeva, K. V.
    Mal'kina, A. G.
    Afonin, A. V.
    Muzalevskii, V. M.
    Nenaidenko, V. G.
    Trofimov, B. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (12) : 1857 - 1860
12345