Synthesis of New Tetrazole Derivatives of Spiro‐ and Bis‐barbiturates. Issue 11 (8th October 2015)

• Record Type: Journal Article
• Authors: Kashani, Elmira; Pesyan, Nader Noroozi; Sahin, Ertan
• Is Part Of: Journal of the Chinese Chemical Society. Volume 62:Issue 11(2015:Nov.)
• Page Start: 959
• Page End: 967
• Publication Date: 2015-10-08
• Subjects: Tetrazole -- Spiro‐barbiturates -- 4‐(1H‐Tetrazol‐5‐yl) benzaldehyde -- Intramolecular hydrogen bonding -- Intermolecular hydrogen bonding -- X‐ray; Chemistry -- Periodicals; Electronic journals; 540.5
• DOI: 10.1002/jccs.201500257
• Languages: English
• ISSNs: 0009-4536

Abstract

Abstract: This work described the synthesis of the first and unprecedented examples of 5‐aryl‐1 H ‐tetrazoles including spiro‐ and bis‐(thio)barbiturates, generated from the reaction between 4‐(1 H ‐tetrazol‐5‐yl)benzaldehyde with (thio)barbituric acids and cyanogen bromide (BrCN) in the presence of triethylamine, providing good overall yields. Tetrazoles based on bis‐(thio) barbiturates were also obtained in the absence of BrCN under the same conditions. The structures were characterized by IR, 1 H NMR, 13 C NMR, X‐ray crystallography and mass analysis techniques. The reaction mechanism was proposed. The hydrogen bond strength (EHB ) versus d (O1⋅⋅⋅⋅⋅O7 (w)) distance (kcal.mol −1 ) and corresponding pKa value for the proton of H3A (in water molecule) in4b.H2 O were estimated to be 13.8 kcal.mol −1 and 8.2, respectively. Abstract : The first and unprecedented examples of 5‐aryl‐1 H ‐tetrazoles including spiro‐ and bis‐(thio)barbiturates were synthesized, providing in good overall yields new type tetrazoles. The hydrogen bond strength (EHB ) versus d (O1⋅⋅⋅⋅⋅O7 (w)) distance (kcal.mol −1 ) and corresponding pKa value for the proton of H3A (in water molecule) in 4b.H2 O were estimated to be 13.8 kcal.mol −1 and 8.2, respectively.