title: A synthetic method to access symmetric and non-symmetric 2-(N,N'-disubstituted)guanidinebenzothiazoles.
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-carbonodithioimidate 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.
authors.affiliation: 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. alecruz@ipn.mx
authors.forename: Alejandro
authors.initials: A
authors.lastname: Cruz
authors.forename: Itzia I
authors.initials: II
authors.lastname: Padilla-Martínez
authors.forename: Efrén V
authors.initials: EV
authors.lastname: García-Báez
mesh_terms: D000641:Ammonia / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008744:Methylamines / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000814:Aniline Compounds; D052160:Benzothiazoles; D006146:Guanidines; D008744:Methylamines; D011759:Pyrrolidines; D000641:Ammonia; C027451:methylamine; C032519:pyrrolidine; C023650:aniline