Dithiocarbamates, thiocarbamic esters, dithiocarboimidates, guanidines, thioureas, isothioureas, and tetraazathiapentalene derived from 2-aminobenzothiazole

Fabiola Téllez, Alejandro Cruz, Horacio López-Sandoval, Iris Ramos-García, Martha Gayosso, R. Nely Castillo-Sierra, Brenda Paz-Michel, Heinrich Nöth, Angelina Flores-Parra, Rosalinda Contreras

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Abstract

Reactions between CS2 and the exocyclic amino groups of 2-aminobenzothiazoles gave series of molecules bearing thiourea, isothiourea, dithiocarbamate, dithiocarboimine, dimethyldithiocarbamate, methyldithiocarbamate, S-CH3 and O-alkyl thiocarbarnic ester, and guanidine groups. Preferred tautomers and conformers were determined. Most compounds present coordinative bonds between the endocyclic sulfur atom, which behaves as a Lewis acid, and oxygen, nitrogen, and sulfur acting as bases. A new dibenzothiazolyltetraazathiapentalene containing a T-shaped hypervalent sulfur atom and displaying "single bond-no bond resonance" is discussed. X-ray structures of eleven compounds are reported. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Original languageAmerican English
Pages (from-to)4203-4214
Number of pages3781
JournalEuropean Journal of Organic Chemistry
DOIs
StatePublished - 11 Oct 2004
Externally publishedYes

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Téllez, F., Cruz, A., López-Sandoval, H., Ramos-García, I., Gayosso, M., Nely Castillo-Sierra, R., Paz-Michel, B., Nöth, H., Flores-Parra, A., & Contreras, R. (2004). Dithiocarbamates, thiocarbamic esters, dithiocarboimidates, guanidines, thioureas, isothioureas, and tetraazathiapentalene derived from 2-aminobenzothiazole. European Journal of Organic Chemistry, 4203-4214. https://doi.org/10.1002/ejoc.200400305