caa a22 4500 445875755 CHVBK 20180317145527.0 cr unu---uuuuu 170323e20110901xx s 000 0 eng 10.1007/s10593-011-0831-z doi (NATIONALLICENCE)springer-10.1007/s10593-011-0831-z Cyclocondensation of n-(prop-2-yn-1-yl)- and n-(penta-2,4-diyn-1-yl)- o -phenylenediamines with phenyl isothiocyanate and carbon disulfide [Elektronische Daten] [R. Novikov, N. Danilkina, I. Balova] The cyclocondensation of N-(prop-2-yn-1-yl)-o-phenylenediamines with phenyl isothiocyanate leads to the formation of 1-(prop-2-yn-1-yl)-1,3-dihydro-2H-benzimidazole-2-thiones irrespective of the substituent nature at the triple bond. Reactions of both mono- and diacetylenic derivatives of o-phenylenediamine with carbon disulfide in the presence of KOH proceed with the formation of two heterocyclic nuclei simultaneously. From N-(prop-2-yn-1-yl)-o-phenylenediamines containing an aryl substituent at the triple bond, and N-(penta-2,4-diyn-1-yl)-o-phenylenediamines 2-methylidene-2,3-dihydro[1,3]thiazolo[3,2-a]benzimidazoles are formed. The latter are readily isomerized under the action of base giving thiazolo[3,2-a]benzimidazoles. The cyclocondensation of N-(alk-2-yn-1-yl)-o-phenylenediamines with CS2 leads to [1,3]thiazino[3,2-a]benzimidazoles. Springer Science+Business Media, Inc., 2011 1-(3-arylprop-2-yn-1-yl)-1,3-dihydro-2H-benzimidazole-2-thiones nationallicence N-(penta-2,4-diyn-1-yl)- o -phenylenediamines nationallicence N-(prop-2-yn-1-yl)- o -phenylenediamines nationallicence carbon disulfide nationallicence [1,3]thiazolo[3,2- a ]- benzimidazoles nationallicence phenyl isothiocyanate nationallicence cyclocondensation nationallicence Novikov R. Saint-Petersburg State University, 26 Universitetskiy Pr., 198504, Saint Petersburg, Russia aut Danilkina N. Saint-Petersburg State University, 26 Universitetskiy Pr., 198504, Saint Petersburg, Russia aut Balova I. Saint-Petersburg State University, 26 Universitetskiy Pr., 198504, Saint Petersburg, Russia aut Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 47/6(2011-09-01), 758-766 0009-3122 47:6<758 2011 47 10593 https://doi.org/10.1007/s10593-011-0831-z text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10593-011-0831-z text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Novikov R. Saint-Petersburg State University, 26 Universitetskiy Pr., 198504, Saint Petersburg, Russia aut NATIONALLICENCE 700 1- Danilkina N. Saint-Petersburg State University, 26 Universitetskiy Pr., 198504, Saint Petersburg, Russia aut NATIONALLICENCE 700 1- Balova I. Saint-Petersburg State University, 26 Universitetskiy Pr., 198504, Saint Petersburg, Russia aut NATIONALLICENCE 773 0- Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 47/6(2011-09-01), 758-766 0009-3122 47:6<758 2011 47 10593 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer