1,3,4-Thiadiazoles and 1,3-thiazoles from one-pot reaction of bisthioureas with 2-(bis(methylthio)methylene)malononitrile and ethyl 2-cyano-3,3-bis(methylthio)acrylate

被引:17
作者
Aly, Ashraf A. [1 ]
Hassan, Alaa A. [1 ]
Braese, Stefan [2 ]
Ibrahim, Mahmoud A. A. [1 ]
Abd Al-Latif, El-Shimaa S. M. [1 ]
Spuling, Eduard [2 ]
Nieger, Martin [3 ]
机构
[1] Menia Univ, Dept Chem, Fac Sci, El Minia 61519, Egypt
[2] Karlsruhe Inst Technol, Inst Organ Chem, Karlsruhe, Germany
[3] Univ Helsinki, Dept Chem, Inorgan Chem Lab, Helsinki, Finland
关键词
Bisthioureas; bis(methylthio)malononitrile; bis(methylthio)acrylate; 1; 3; 4-thiadiazoles; 3-thiazoles; X-ray; DERIVATIVES;
D O I
10.1080/17415993.2016.1237637
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Bisthioureas reacted with either 2-(bis(methylthio)methylene)malononitrile or ethyl 2-cyano-3,3-bis(methylthio)acrylate to give 1,3,4-thiadiazoles and 1,3-thiazoles. Only, the reactive allyl derivative of bisthioureas reacted with the bis(methylthio)methylene compounds to give 1,3-thiazoles. The mechanism was discussed. The structures of products were proved by MS, IR, NMR and elemental analyses and X-ray structure analysis. [GRAPHICS]
引用
收藏
页码:69 / 75
页数:7
相关论文
共 17 条
[1]   Thiosugar nucleosides. Synthesis and biological activity of 1,3,4-thiadiazole, thiazoline and thiourea derivatives of 5-thio-D-glucose [J].
Al-Masoudi, NA ;
Al-Soud, YA ;
Al-Masoudi, WA .
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2004, 23 (11) :1739-1749
[2]   Design, synthesis and biological evaluation of some novel benzylidene-2-(4-phenylthiazol-2-yl) hydrazines as potential anti-inflammatory agents [J].
Bharti, Sanjay Kumar ;
Singh, Sushil Kumar .
MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (02) :1004-1015
[3]   1,3,4-OXADIAZOLE, 1,3,4-THIADIAZOLE, AND 1,2,4-TRIAZOLE ANALOGS OF THE FENAMATES - IN-VITRO INHIBITION OF CYCLOOXYGENASE AND 5-LIPOXYGENASE ACTIVITIES [J].
BOSCHELLI, DH ;
CONNOR, DT ;
BORNEMEIER, DA ;
DYER, RD ;
KENNEDY, JA ;
KUIPERS, PJ ;
OKONKWO, GC ;
SCHRIER, DJ ;
WRIGHT, CD .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (13) :1802-1810
[4]  
Brase S, 2015, PRIVILEGED SCAFFOLDS
[5]   2-aminothiazole as a novel kinase inhibitor template.: Structure-activity relationship studies toward the discovery of N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl)]-2-methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide (Dasatinib, BMS-354825) as a potent pan-Src kinase inhibitor [J].
Das, Jagabandhu ;
Chen, Ping ;
Norris, Derek ;
Padmanabha, Ramesh ;
Lin, James ;
Moquin, Robert V. ;
Shen, Zhongqi ;
Cook, Lynda S. ;
Doweyko, Arthur M. ;
Pitt, Sidney ;
Pang, Suhong ;
Shen, Ding Ren ;
Fang, Qiong ;
de Fex, Henry F. ;
McIntyre, Kim W. ;
Shuster, David J. ;
Gillooly, Kathleen M. ;
Behnia, Kamelia ;
Schieven, Gary L. ;
Wityak, John ;
Barrish, Joel C. .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (23) :6819-6832
[6]   Drugs anti-HIV: Past, present and future perspectives. [J].
de Souza, MVN ;
de Almeida, MV .
QUIMICA NOVA, 2003, 26 (03) :366-372
[7]   Nitazoxanide: A new thiazolide antiparasitic agent [J].
Fox, LM ;
Saravolatz, LD .
CLINICAL INFECTIOUS DISEASES, 2005, 40 (08) :1173-1180
[8]   Desulfurization Strategy in the Construction of Azoles Possessing Additional Nitrogen, Oxygen or Sulfur using a Copper(I) Catalyst [J].
Guin, Srimanta ;
Rout, Saroj Kumar ;
Gogoi, Anupal ;
Nandi, Shyamapada ;
Ghara, Krishna Kanta ;
Patel, Bhisma K. .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (14-15) :2757-2770
[9]   Synthesis of 1,3,4-thiadiazole, 1,3,4-thiadiazine, 1,3,6-thiadiazepane and quinoxaline derivatives from symmetrical dithiobiureas and thioureidoethylthiourea derivatives [J].
Hassan, AA ;
Mourad, AFE ;
El-Shaieb, KM ;
Abou-Zied, AH .
MOLECULES, 2005, 10 (07) :822-832
[10]  
Heinz E, 1994, SOFW-J, V120, P286