{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,9]],"date-time":"2026-03-09T07:20:33Z","timestamp":1773040833806,"version":"3.50.1"},"reference-count":31,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2012,7,17]],"date-time":"2012-07-17T00:00:00Z","timestamp":1342483200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A series of benzimidazole-2-thione derivatives was synthesized using a reaction between the macrocyclic aminal 16H,13H-5:12,7:14-dimethanedibenzo[d,i]-[1,3,6,8] tetraazecine (DMDBTA, 5) and various nucleophiles in the presence of carbon disulfide. A full chemical characterization using IR, 1H-, 13C-NMR and GC-MS analyses of the new compounds is provided. These compounds were separated from the reaction mixture by column chromatography (CC) in highly pure form in 15%\u201351.4% yield.<\/jats:p>","DOI":"10.3390\/molecules17078578","type":"journal-article","created":{"date-parts":[[2012,7,17]],"date-time":"2012-07-17T12:25:04Z","timestamp":1342527904000},"page":"8578-8586","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["A Facile and Efficient Procedure for the Synthesis of New Benzimidazole-2-thione Derivatives"],"prefix":"10.3390","volume":"17","author":[{"given":"Augusto","family":"Rivera","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, Universidad Nacional de Colombia, Sede Bogot\u00e1, Cra.30 No.45-03, Bogot\u00e1 111321, Colombia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mauricio","family":"Maldonado","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, Universidad Nacional de Colombia, Sede Bogot\u00e1, Cra.30 No.45-03, Bogot\u00e1 111321, Colombia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jaime","family":"R\u00edos-Motta","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, Universidad Nacional de Colombia, Sede Bogot\u00e1, Cra.30 No.45-03, Bogot\u00e1 111321, Colombia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2012,7,17]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1002\/cber.18750080136","article-title":"Noch einige Bemerkungen \u00fcber Senf\u00f6le","volume":"8","author":"Hofmann","year":"1875","journal-title":"Ber. Dtsch. Chem. Ges."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1080\/17415990701245107","article-title":"Reactions of carbon disulfide with Nnucleophiles","volume":"28","year":"2007","journal-title":"J. Sulfur Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"2706","DOI":"10.1021\/ja01263a051","article-title":"Complex Formations between iodine and \u03bc-mercapto-dihydroglyoxalines","volume":"64","author":"Johnson","year":"1942","journal-title":"J. Am. Chem. Soc."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"3688","DOI":"10.1021\/ie00038a003","article-title":"Reaction of carbon disulfide and o-phenylenediamine catalyzed by tertiary amine in a homogeneous solution","volume":"34","author":"Wang","year":"1995","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"85","DOI":"10.1016\/j.jcice.2006.04.002","article-title":"Homogeneous catalyzed reaction of carbon disulfide and o-phenylenediamine by tetrabutylammonium hydroxide in the presence of potassium hydroxide","volume":"38","author":"Wang","year":"2007","journal-title":"J. Chin. Inst. Chem. Eng."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"139","DOI":"10.1016\/0022-0728(91)85257-P","article-title":"The formation of an effective anti-corrosion film on copper surfaces from 2-mercaptobenzimidazole solution","volume":"310","author":"Xue","year":"1991","journal-title":"J. Electroanal. Chem. Interfacial Electrochem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1647","DOI":"10.1016\/S0010-938X(98)00060-2","article-title":"Characterization and mechanism of direct film formation on a Cu electrode through electro-oxidation of 1-mercaptobenzimidazole","volume":"40","author":"Perrin","year":"1998","journal-title":"Corros. Sci."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"767","DOI":"10.1016\/S0301-679X(98)00099-1","article-title":"Tribological study of a Mannich compound of 2-mercaptobenzimidazole in liquid paraffin","volume":"31","author":"Zhang","year":"1998","journal-title":"Tribol. Int."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/S0043-1648(99)00111-8","article-title":"The effect of molecular structure of heterocyclic compounds containing N, O and S on their tribological performance","volume":"231","author":"Zhang","year":"1999","journal-title":"Wear"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1007\/BF01244293","article-title":"Adsorption of Cu(II), Zn(II), Cd(II), Hg(II) and Pb(II) from aqueous solutions on a 2-mercaptobenzimidazole-modified silica gel","volume":"102","author":"Moreira","year":"1990","journal-title":"Microchim. Acta"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"539","DOI":"10.1080\/00304940509354982","article-title":"Synthesis of 2-mercaptobenzothiazole and of 2-mercaptobenzimidazole derivatives using polymer-supported anions","volume":"37","author":"Dalal","year":"2005","journal-title":"Org. Prep. Proced. Int."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"524","DOI":"10.1021\/jm00226a016","article-title":"Synthesis of heterocyclic fused thiazole acetic acids 2","volume":"19","author":"Bell","year":"1976","journal-title":"J. Med. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"3238","DOI":"10.1016\/j.bmcl.2009.04.088","article-title":"Novel 1-(2-aminopyrazin-3-yl)methyl-2-thioureas as potent inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2)","volume":"19","author":"Lin","year":"2009","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1080\/17415990601055291","article-title":"Synthesis of 2-mercaptobenzothiazole and 2-mercaptobenzimidazole derivatives condensed with carbohydrates as a potential antimicrobial agents","volume":"28","author":"Cardoso","year":"2007","journal-title":"J. Sulfur Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"8271","DOI":"10.1016\/j.bmc.2006.09.017","article-title":"Green route for the heterocyclization of 2-mercaptobenzimidazole into \u03b2-lactum segment derivatives containing -CONH-bridge with benzimidazole: Screening in vitro antimicrobial activity with various microorganisms","volume":"14","author":"Desai","year":"2006","journal-title":"Bioorg. Med. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1111\/j.1470-8744.1997.tb00429.x","article-title":"Effects of derivatives of 2-mercaptobenzimidazole on polyketide biosynthesis in Penicillium frequentans","volume":"25","author":"Proksa","year":"1997","journal-title":"Biotechnol. Appl. Biochem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"9402","DOI":"10.1021\/ic061115s","article-title":"Synthesis of 1D {Cu6(\u03bc3-SC3H6N2)4(\u03bc-SC3H6N2)2(mu-I)2I4}n and 3D {Cu2(\u03bc-SC3H6N2)2(\u03bc-SCN)2}n polymers with 1,3-imidazolidine-2-thione: Bond isomerism in polymers","volume":"45","author":"Lobana","year":"2006","journal-title":"Inorg. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1914","DOI":"10.1021\/ic0484809","article-title":"Versatility of heterocyclic thioamides in the construction of a trinuclear cluster [Cu3I3(dppe)3 (SC5H4NH)] and Cu(I) linear polymers {Cu6(SC5H4NH)6I6}nx2nCH3CN and {Cu(I)6 (SC3H6N2)6X6}n (X = Br, I)","volume":"44","author":"Lobana","year":"2005","journal-title":"Inorg. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"2967","DOI":"10.1016\/j.ica.2007.02.009","article-title":"Synthesis, crystal structures, and spectroscopic characterization of the neutral monomeric tetrahedral [M(Diap)2(OAc)2]H2O complexes (M = Zn, Cd; Diap = 1,3-diazepane-2-thione; OAc = acetate) with N-H\u2026O and O-H\u2026O intra- and intermolecular hydrogen bonding interactions","volume":"360","author":"Beheshti","year":"2007","journal-title":"Inorg. Chim. Acta"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1515\/HC.2004.10.1.77","article-title":"Nucleophilic substitution at the aminalic carbon of some macrocyclic polyaminals","volume":"10","author":"Rivera","year":"2004","journal-title":"Heterocycl. Commun."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"7467","DOI":"10.1016\/j.tetlet.2006.08.045","article-title":"Unexpected behavior of 6H,13H-5:12,7:14-dimethane-dibenzo[d,i][1,3,6,8]tetraazecine (DMDBTA) toward phenols","volume":"47","author":"Rivera","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1651","DOI":"10.3987\/COM-08-11333","article-title":"Solvent-Free Synthesis of 2-(1H-benzimidazol-1-yl-methyl)-4-substituted-1-hydroxyaryl by the two component Mannich reaction between 6H,13H-5:12,7:14-Dimethanedibenzo[d,i][1,3,6,8]tetraazecine (DMDBTA) and phenols","volume":"75","author":"Rivera","year":"2008","journal-title":"Heterocycles"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"588","DOI":"10.1016\/j.saa.2009.07.009","article-title":"FT-IR and DFT studies of the proton affinity of small aminal cages","volume":"74","author":"Rivera","year":"2009","journal-title":"Spectrochim. Acta A"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"102","DOI":"10.1016\/j.tetlet.2009.10.094","article-title":"Novel access to 1-substituted-benzimidazoles via benzotriazole-mediated synthesis","volume":"51","author":"Rivera","year":"2010","journal-title":"Tetrahedron Lett."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"952","DOI":"10.1021\/jo01158a004","article-title":"Reactions of mono- and di-amines with carbon disulphide. II. Methylenediamine and imidazolidine-carbon disulphide reactions","volume":"14","author":"Donia","year":"1949","journal-title":"J. Org. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"128","DOI":"10.1016\/j.vibspec.2009.12.001","article-title":"Infrared, Raman and temperature-dependent NMR spectra, vibrational assignments, normal coordinate analysis, and DFT calculations of benzoxazoline-2-thione","volume":"52","author":"Mohamed","year":"2010","journal-title":"Vib. Spectrosc."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"4315","DOI":"10.1016\/j.tetlet.2005.04.101","article-title":"A simple and efficient procedure for the synthesis of benzimidazoles using air as the oxidant","volume":"46","author":"Lin","year":"2005","journal-title":"Tetrah edron Lett."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"8025","DOI":"10.1016\/j.tetlet.2006.09.061","article-title":"Parallel solution-phase synthesis of substituted 2-(1,2,4-triazol-3-yl)benzimidazoles","volume":"47","author":"Ivanova","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"119","DOI":"10.1016\/j.carres.2006.10.019","article-title":"One-pot synthesis of 2-C-glycosylated benzimidazoles from the corresponding methanal dimethyl acetals","volume":"342","author":"Vojtech","year":"2007","journal-title":"Carbohydr. Res."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"8739","DOI":"10.1021\/jo049197u","article-title":"Mild and selective reduction of imines: Formation of an unsymmetrical macrocycle","volume":"69","author":"Gallant","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref_31","first-page":"o1135","article-title":"1,3-bis(ethoxymethyl)-1H-benzimidazole-2(3H)-thione","volume":"E 66","author":"Rivera","year":"2010","journal-title":"Acta Cryst."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/17\/7\/8578\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T21:51:18Z","timestamp":1760219478000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/17\/7\/8578"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,7,17]]},"references-count":31,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2012,7]]}},"alternative-id":["molecules17078578"],"URL":"https:\/\/doi.org\/10.3390\/molecules17078578","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,7,17]]}}}