Synthesis of Pyrrolidine-Fused 1,3-Dithiolane Oligomers by the Cycloaddition of Polycyclic Dithiolethiones to Maleimides and Evaluation as Mercury(II) Indicators

被引:8
作者
Fuertes, Pedro [1 ]
Garcia-Valverde, Maria [1 ]
Cuevas, Jose V. [1 ]
de Grenu, Borja Diaz [1 ]
Rodriguez, Teresa [1 ]
Rojo, Josefa [1 ]
Torroba, Tomas [1 ]
机构
[1] Univ Burgos, Fac Sci, Dept Chem, Burgos 09001, Spain
关键词
ELECTRONIC COMMUNICATION; CHEMISTRY; TETRATHIAFULVALENES; DERIVATIVES; POLYIMIDES; ANALOGS; COMPLEX; DONORS; CROWN;
D O I
10.1021/jo500076c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The scandium triflate-catalyzed cycloaddition reaction of polycyclic 1,2-dithiolethiones to maleimides is described. The reaction constitutes an easy approach to linear as well as branched oligomeric cis-fused dihydro [1,3]dithiolo[4,5-c]pyrrole-4,6-dione rings interconnected by 3,5-diylidenethiomorpholine-2,6-dithione or ylidene-6-thioxo[1,2]dithiolo[3,4-b][1,4]thiazin-3-one groups. The presence of highly colored, highly polarized push pull alpha,beta-unsaturated thione groups in their structures make these compounds sensitive to the presence of mercury(II) cation in organic or mixed organic/aqueous solvents.
引用
收藏
页码:2213 / 2225
页数:13
相关论文
共 65 条
[1]   SYNTHESIS OF NORBORNANE-FUSED 1,3-DITHIOLANES AND EVALUATION OF 1,3-DITHIOLANE-CONTAINING POLYMERS AS ABSORBANTS FOR MERCURY(II) SALTS [J].
Aitken, R. Alan ;
Aitken, Kati M. ;
Lambert, Stuart ;
Playfair, Richard ;
Wilson, Neil J. .
HETEROCYCLES, 2012, 84 (02) :1113-1122
[2]   Cycloaddition of Bu3P center dot CS2: Formation of extended bis- and tris-1,3-dithiolanes and dithiolane-containing polymers [J].
Aitken, RA ;
Hill, L ;
Massil, T ;
Hursthouse, MB ;
Malik, KMA .
TETRAHEDRON, 1997, 53 (30) :10441-10450
[3]   POLYIMIDES BY DIELS-ALDER POLYADDITION OF ALPHA-PYRONES [J].
ALHAKIMI, G ;
GORLS, H ;
KLEMM, E .
MACROMOLECULAR CHEMISTRY AND PHYSICS, 1994, 195 (05) :1569-1576
[4]   SYNTHESIS OF NEW POLYIMIDES BY DIELS-ALDER REACTION OF BIS(2-PYRONE)S WITH BISMALEIMIDES [J].
ALHAKIMI, G ;
KLEMM, E ;
GORLS, H .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1995, 33 (07) :1133-1142
[5]   DFT Study of Thermal 1,3-Dipolar Cycloaddition Reactions between Alkynyl Metal(0) Fischer Carbene Complexes and 3H-1,2-Dithiole-3-thione Derivatives [J].
Andrada, Diego M. ;
Granados, Alejandro M. ;
Sola, Miquel ;
Fernandez, Israel .
ORGANOMETALLICS, 2011, 30 (03) :466-476
[6]   Decreased Optical Nonlinearities upon CF3 Substitution on Tricyanofuran Acceptors [J].
Andreu, Raquel ;
Angel Cerdan, Miguel ;
Franco, Santiago ;
Garin, Javier ;
Belen Marco, Ana ;
Orduna, Jesus ;
Palomas, David ;
Villacampa, Belen ;
Alicante, Raquel ;
Allain, Magali .
ORGANIC LETTERS, 2008, 10 (21) :4963-4966
[7]   Synthesis of highly branched sulfur-nitrogen heterocycles by cascade cycloadditions of [1,2]dithiclo[1,4]thiazines and [1,2]dithiolopyrroles [J].
Barriga, S ;
Fuertes, P ;
Marcos, CF ;
Torroba, T .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (11) :3672-3682
[8]   Synthesis of [1,3]dithiole and spiro[1,3]dithiole thiopyran derivatives of the [1,2]dithiolo[1,4]thiazine ring system [J].
Barriga, S ;
Fuertes, P ;
Marcos, CF ;
Rakitin, OA ;
Torroba, T .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (18) :6439-6448
[9]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[10]   ExTTF-Based Dyes Absorbing over the Whole Visible Spectrum [J].
Bouit, Pierre-Antoine ;
Villegas, Carmen ;
Luis Delgado, Juan ;
Viruela, Pedro M. ;
Pou-Amerigo, Rosendo ;
Orti, Enrique ;
Martin, Nazario .
ORGANIC LETTERS, 2011, 13 (04) :604-607