Facile and Convenient Synthesis of New Thieno[2,3-b]-Thiophene Derivatives.docVIP

Molecules 2010, 15, 9418-9426; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Facile and Convenient Synthesis of New Thieno[2,3-b]- Thiophene Derivatives Yahia Nasser Mabkhot 1,*, Nabila abd Elshafy Kheder 2,? and Abdullah Mohammad Al-Majid 1 1 Department of Chemistry, Faculty of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia 2 Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt ? Current Address: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, King Khalid University, Abha, Saudi Arabia; E-Mail: nabila_abdelshafy@. * Author to whom correspondence should be addressed; E-Mail: yahia@.sa. Received: 12 October 2010; in revised form: 15 December 2010 / Accepted: 16 December 2010 / Published: 20 December 2010 Abstract: A facile and convenient synthesis of bis(2-(1H-benzo[d]imidazol-2(3H)- ylidene)-3-oxopropanenitrile), bis((3-amino-5-(methylthio)-1H-pyrazol-4-yl)methanone) and bis(2-thioxo-1,2-dihydropyrimidine-5-carbonitrile) derivatives incorporating a thieno- [2,3-b]thiophene moiety via versatile, readily accessible diethyl 3,4-dimethylthieno-[2,3- b]thiophene-2,5-dicarboxylate (1) is described. Keywords: thieno[2,3-b]thiophene; bis-heterocycles; nucleophilic addition; 2-bromo-1-phenylethanone 1. Introduction Recently, bis(heterocycles) have received a great deal of attention, not only as model compounds for main chain polymers but also because many biologically active natural and synthetic products have molecular symmetry [1-8]. On the other hand, many thiophene-containing compounds, including annulated compounds, exhibit biological activities [9,10]. Thienothiophene derivatives have been developed for different purposes in the pharmaceutical field and have been tested as potential antitumor, antiviral and antibiotic, antiglaucoma drugs, or as inhibitors of platelet aggregation [11-15