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Molecules 2012, 17(9), 10178-10191; doi:10.3390/molecules170910178
Article

A Synthetic Method to Access Symmetric and Non-Symmetric 2-(N,N'-disubstituted)guanidinebenzothiazoles

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Received: 26 June 2012 / Revised: 14 August 2012 / Accepted: 15 August 2012 / Published: 24 August 2012
(This article belongs to the Section Organic Synthesis)
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Abstract

Symmetric and non-symmetric 2-(N-H, N-methyl, N-ethylenyl and N-aryl)guanidinebenzothiazoles were synthesized from the reaction of ammonia, methylamine, pyrrolidine and aniline with dimethyl benzo[d]thiazol-2-yl-carbono-dithioimidate (5) as intermediate. The products were characterized by 1H-, 13C-NMR spectroscopy and three of them by X-ray diffraction analysis. HN-phenyl protons formed intramolecular hydrogen bonds that assist the stereochemistry of the second substituent, whereas the HN-alkyl protons were involved in intermolecular hydrogen bonding.
Keywords: 2-aminobenzothiazole; dithiomethylcarboimidate; isothiourea; benzothiazole; guanidine 2-aminobenzothiazole; dithiomethylcarboimidate; isothiourea; benzothiazole; guanidine
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Cruz, A.; Padilla-Martínez, I.I.; García-Báez, E.V. A Synthetic Method to Access Symmetric and Non-Symmetric 2-(N,N'-disubstituted)guanidinebenzothiazoles. Molecules 2012, 17, 10178-10191.

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