ONE-POT SYNTHESIS OF NOVEL RHODANINE BASED KETENIMINES VIA MULTICOMPONENT REACTIONS

被引:7
作者
Baharfar, Robabeh [1 ]
Porahmad, Nasim [1 ]
机构
[1] Univ Mazandaran, Dept Chem, Babol Sar, Iran
关键词
Alkyl isocyanides; dialkyl acetylenedicarboxylates; 5-(4-dimethylaminobenzylidene)-rhodanine; ketenimines; rhodanine; three-component reaction; TERT-BUTYL ISOCYANIDE; DIALKYL ACETYLENEDICARBOXYLATES; ACETYLENIC ESTERS; INHIBITORS; CONSTRUCTION; DERIVATIVES;
D O I
10.1080/10426507.2011.557418
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Synthesis of polyfunctionalized ketenimines via three-component reactions of rhodanine and 5-(4-dimethylaminobenzylidene)-rhodanine with dialkyl acetylenedicarboxylates and alkyl isocyanides is described. The reactions proceed smoothly under mild conditions leading to the desired products in good yields. In the case of methyl acetylenecarboxylate, the reaction led to methyl (Z)-3-({5-[(E)-1-(tert-butylamino)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl}sulfanyl)-2-propenoate in low yield.
引用
收藏
页码:1988 / 1996
页数:9
相关论文
共 33 条
[11]   An efficient multicomponent transformation of alkyl isocyanides, dialkyl acetylenedicarboxylates, and 2,4-dihydroxybenzophenones or 2,4-dihydroxyacetophenones into 2-amino-4H-chromene derivatives [J].
Baharfar, Robabeh ;
Vahdat, Seyed Mohammad ;
Ahmadian, Majid ;
Taghizadeh, Mohammad Javad .
MONATSHEFTE FUR CHEMIE, 2010, 141 (02) :213-218
[12]   Inhibition of clinically relevant mutant variants of HIV-1 by quinazolinone non-nucleoside reverse transcriptase inhibitors [J].
Corbett, JW ;
Ko, SS ;
Rodgers, JD ;
Gearhart, LA ;
Magnus, NA ;
Bacheler, LT ;
Diamond, S ;
Jeffrey, S ;
Klabe, RM ;
Cordova, BC ;
Garber, S ;
Logue, K ;
Trainor, GL ;
Anderson, PS ;
Erickson-Viitanen, SK .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (10) :2019-2030
[13]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[14]  
2-U
[15]   Identification of selective inhibitors for the glycosyltransferase via high-throughput murG screening [J].
Hu, Y ;
Heim, JS ;
Chen, L ;
Ginsberg, C ;
Gross, B ;
Kraybill, B ;
Tiyanont, K ;
Fang, X ;
Wu, T ;
Walker, S .
CHEMISTRY & BIOLOGY, 2004, 11 (05) :703-711
[16]   Insecticidal and antifungal activities of aminorhodanine derivatives [J].
Inamori, Y ;
Okamoto, Y ;
Takegawa, Y ;
Tsujibo, H ;
Sakagami, Y ;
Kumeda, Y ;
Shibata, M ;
Numata, A .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1998, 62 (05) :1025-1027
[17]  
Litvinov V.P., 2003, Russ. Chem. Rev, V72, P69, DOI [DOI 10.1070/RC2003V072N01ABEH000764, 10.1070/RC2003v072n01ABEH000764]
[18]   THE USE OF ISOCYANIDES IN HETEROCYCLIC SYNTHESIS - A REVIEW [J].
MARCACCINI, S ;
TORROBA, T .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1993, 25 (02) :141-208
[19]   Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes [J].
Nair, V ;
Rajesh, C ;
Vinod, AU ;
Bindu, S ;
Sreekanth, AR ;
Mathen, JS ;
Balagopal, L .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (12) :899-907
[20]   Multicomponent reactions involving zwitterionic intermediates for the construction of heterocyclic systems: one pot synthesis of aminofurans and iminolactones [J].
Nair, V ;
Vinod, AU ;
Abhilash, N ;
Menon, RS ;
Santhi, V ;
Varma, RL ;
Viji, S ;
Mathew, S ;
Srinivas, R .
TETRAHEDRON, 2003, 59 (51) :10279-10286