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
来源：
JOURNAL OF SULFUR CHEMISTRY | 2012年 / 33卷 / 01期
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
  • [31] Synthesis of 1,2,4-Trithiolanes from Thione S-Oxides and Lawesson Reagent at Room Temperature
    Okuma, Kentaro
    Shigetomi, Toshiyuki
    Shibata, Shinji
    Shioji, Kosei
    1600, Chemical Society of Japan (77):
  • [32] SYNTHESIS OF NOVEL FUSED 2-AMINOBENZOTHIAZOLE DERIVATIVES
    Rajitha, Ch
    Vineel, B. George
    Venkataiah, S.
    Dubey, P. K.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 24 (02) : 111 - 114
  • [33] 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
  • [34] TITRATIONS IN NONAQUEOUS MEDIA .5. ACID-BASE BEHAVIOR OF SUBSTITUTED 2-AMINO-3-CYANOFURANS, 2-AMINO-3-CYANOTHIOPHENES AND 2-AMINO-3-CYANOPYRROLE AND THEIR SCHIFF-BASES WITH SALICYLALDEHYDE AND 2-HYDROXY-1-NAPHTHALDEHYDE
    GUNDUZ, T
    KILIC, E
    ERTUZUN, V
    CETINEL, G
    ANALYST, 1986, 111 (12) : 1439 - 1442
  • [35] Synthesis of Novel 2, 3′-Bipyrrole Derivatives from Chalcone and Amino Acids as Antitumor Agents
    Kalmouch, Atef
    Radwan, Mohamed A. A.
    Omran, Mervat M.
    Sharaky, Marwa
    Moustafa, Gaber O.
    EGYPTIAN JOURNAL OF CHEMISTRY, 2020, 63 (11): : 4409 - 4421
  • [36] Synthesis of 2,5-diaryl-1,3,4-thiadiazoles via Lawesson's reagent under microwave irradiation
    Huang, HM
    Yu, HT
    Chen, PL
    Han, J
    Meng, JB
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2004, 24 (05) : 502 - 505
  • [37] Stereospecific thionation of 2-ethoxy-1,2-oxaphosphorinane 2-oxide and its derivatives with Lawesson's reagent
    Polozov, AM
    Cremer, SE
    Fanwick, PE
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1999, 77 (07): : 1274 - 1280
  • [38] A facile synthesis of 1-alkyl-1,3,2-diazaphospholidin-4-thione-2-sulfide via Lawesson's reagent
    Li, K
    He, LN
    Qing, XH
    Luo, YP
    Ding, MW
    HETEROCYCLIC COMMUNICATIONS, 1999, 5 (02) : 189 - 192
  • [39] The reaction of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulphide (Lawesson's reagent, LR) with some s-triazole derivatives. Synthesis of s-triazole-fused P-heterocycles
    Moustafa, HM
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2000, 164 : 11 - 22
  • [40] Reaction of the Lawesson reagent with gamma-phosphonated hydrazones: Synthesis of new derivatives of delta(5)-3-thioxo-1,2,3-diazaphospholine
    Touil, S
    BenDhia, MT
    Zantour, H
    Baccar, B
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1996, 119 : 295 - 302
12345