Electronic Effect of Substituents Present on Carbonyl Compounds: Analysis of Product Formation in One-Pot Synthesis of 1, 3, 4-thiadiazole Ring
Sheetal B. Marganakop
Department of Studies in Chemistry, Karnatak University, Dharwad – 580003, India and Department of Chemistry, Rani Channamma University, Belagavi, Government First Grade College, Paschapur, Di: Belgaum-591122, India
Ravindra R. Kamble *
Department of Studies in Chemistry, Karnatak University, Dharwad – 580003, India
Gangadhar Y. Meti
Department of Studies in Chemistry, Karnatak University, Dharwad – 580003, India
Mahadev N. Kumbar
Department of Studies in Chemistry, Karnatak University, Dharwad – 580003, India
*Author to whom correspondence should be addressed.
Abstract
Functionalized N-(4-acetyl-5-substituted-4, 5-dihydro-[1, 3, 4]-thiadiazol-2-yl)-acetamides (2a-m) were synthesized by three-fold condensation of carbonyl compound, thiosemicarbazide and acetic anhydride in an one pot three component reaction. In this reaction substituents on carbonyl compounds have played a key role in yield of the product formation. Carbonyl compounds with either electron withdrawing or electron releasing substituents have formed better percentage of products than un-substituted and sterically hindered compounds.
Keywords: Electron donating, electron withdrawing, multicomponent reaction, 1, 3, 4-thiadiazoles, electronic effect, one pot, three components, XRD, Cyclization