a synthetic method to access symmetric and non-symmetric 2-(n,n-disubstituted)guanidinebenzothiazoles合成方法访问对称和非对称2 -(n,n 双取代的)guanidinebenzothiazoles.pdfVIP

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a synthetic method to access symmetric and non-symmetric 2-(n,n-disubstituted)guanidinebenzothiazoles合成方法访问对称和非对称2 -(n,n 双取代的)guanidinebenzothiazoles.pdf

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a synthetic method to access symmetric and non-symmetric 2-(n,n-disubstituted)guanidinebenzothiazoles合成方法访问对称和非对称2 -(n,n 双取代的)guanidinebenzothiazoles

Molecules 2012, 17, 10178-10191; doi:10.3390/molecules170910178 OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article A Synthetic Method to Access Symmetric and Non-Symmetric 2-(N,N-disubstituted)guanidinebenzothiazoles Alejandro Cruz *, Itzia I. Padilla-Martínez and Efrén V. García-Báez Departamento de Ciencias Básicas de la Unidad Profesional Interdisciplinaria de Biotecnología del IPN, Av. Acueducto s/n, Barrio la Laguna Ticomán, México, D.F., 07340, Mexico * Author to whom correspondence should be addressed; E-Mail: alecruz@ipn.mx; Tel.: +5-557-296-000 (ext. 56324); Fax: +5-557-296-000 (ext. 563054). Received: 26 June 2012; in revised form: 14 August 2012 / Accepted: 15 August 2012 / Published: 24 August 2012 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 1. Introduction The guanidine gro