Synthesis of novel fused thienodiazaphosphorine derivatives from 2-amino-3-cyanothiophenes and Lawesson's reagent

被引:11
|
作者
Khalladi, Khaoula [1 ]
Touil, Soufiane [1 ]
机构
[1] Univ Carthage, Dept Chem, Fac Sci Bizerta, Lab Heteroatom Organ Chem, Jarzouna 7021, Tunisia
关键词
thiophenes; diazaphosphorines; Lawesson's reagent; thienodiazaphosphorines; fused heterocycles; Dimroth rearrangement; AMINOPHOSPHONOTHIOPHENE DERIVATIVES; BIOLOGICAL EVALUATION; GEWALD REACTION; 2-OXIDES; REACTIVITY; THIOPHENE; ACIDS;
D O I
10.1080/17415993.2011.639021
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In a simple one-pot procedure, treatment of 2-amino-3-cyanothiophenes with Lawesson's reagent (LR) leads to the new thieno[2,3-d][1,3,2]diazaphosphorine-6-thione-2-sulfides in good to excellent yields. A possible reaction mechanism, involving a Dimroth-type rearrangement, is proposed. The structure of obtained products was confirmed by NMR (H-1, P-31, and C-13) and IR spectroscopies and by mass spectrometry. [GRAPHICS] .
引用
收藏
页码:27 / 32
页数:6
相关论文
共 50 条
  • [1] First Synthesis of Phosphorylated Thienopyridines from 2-amino-3-cyanothiophenes and -ketophosphonates
    Khalladi, Khaoula
    Touil, Soufiane
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2013, 188 (06) : 711 - 718
  • [2] Fluorescent Assembles of 2-Amino-3-cyanothiophenes with Azoles. Design and Peculiar Properties of Absorption and Emission
    Lugovik, Kseniya, I
    Kanaa, Ali
    Benassi, Enrico
    Belskaya, Nataliya P.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (02) : 400 - 411
  • [3] Reaction of Lawesson's reagent with ester hydrazones: synthesis of novel 3-thioxo-1,2,3-diazaphospholine derivatives
    Chebil, Emna
    Touil, Soufiane
    JOURNAL OF SULFUR CHEMISTRY, 2011, 32 (04) : 297 - 302
  • [4] Unexpected synthesis of novel O-ethyl-P-aryl-N-(thiophen-2-yl) phosphonamidothioates from ethyl 2-aminothiophene-3-carboxylates and Lawesson's reagent
    Khalladi, Khaoula
    Touil, Soufiane
    JOURNAL OF SULFUR CHEMISTRY, 2014, 35 (02) : 145 - 151
  • [5] Synthesis of biologically active steroid derivatives by the utility of Lawesson's reagent
    Mohamed, NR
    Elmegeed, GA
    Abd-ElMalek, HA
    Younis, M
    STEROIDS, 2005, 70 (03) : 131 - 136
  • [6] REACTION OF LAWESSON'S REAGENT WITH γ-PHOSPHONYL-OXIMES: SYNTHESIS OF NOVEL 1,2,5-OXAZAPHOSPHOLINE DERIVATIVES
    Wahbi, Aymen
    Touil, Soufiane
    HETEROCYCLES, 2015, 91 (05) : 1017 - 1027
  • [7] A facile synthesis of fused phosphorus-heterocycle with bioactivity via Lawesson's reagent
    He, LN
    Luo, YP
    Li, K
    Yang, GF
    Ding, MW
    Liu, XP
    Wu, TJ
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2002, 177 (11) : 2675 - 2678
  • [8] Reaction of Lawesson's reagent with Mannich base hydrochlorides: synthesis of novel 4H-1,3,2-oxathiaphosphorine-2-sulfide derivatives
    Aouani, Iyadh
    Touil, Soufiane
    JOURNAL OF SULFUR CHEMISTRY, 2014, 35 (02) : 164 - 169
  • [9] Novel synthesis of oxa[9]helicenes by Lawesson's reagent-mediated cyclization of helical quinone derivatives
    Salim, Mohammad
    Akutsu, Akira
    Kimura, Takao
    Minabe, Masahiro
    Karikomi, Michinori
    TETRAHEDRON LETTERS, 2011, 52 (35) : 4518 - 4520
  • [10] A facile synthesis of derivatives of 4-aryl-1,3,2-dioxaphosphorinane-2-sulfide via Lawesson's reagent
    He, LN
    Li, K
    Luo, YP
    Liu, XP
    Ding, MW
    Zhou, QC
    Wu, TJ
    Cai, F
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2000, 156 : 173 - 179