caa a22 4500 605530300 CHVBK 20210128100822.0 cr unu---uuuuu 210128e20150401xx s 000 0 eng 10.1134/S1070428015040168 doi (NATIONALLICENCE)springer-10.1134/S1070428015040168 Fused pyrimidine systems: XV. Intramolecular electrophilic cyclization of 2-allyl(propargyl, cinnamyl)amino-pyrido[2,3- d ]pyrimidin-4(3 H )-ones [Elektronische Daten] [R. Vas'kevich, I. Dyachenko, A. Vas'kevich, E. Rusanov, M. Vovk] 2-(Allylamino)- and 2-(propargylamino)pyrido[2,3-d]pyrimidin-4(3H)-ones underwent intramolecular cyclization on heating in polyphosphoric acid to give angularly fused imidazo[1,2-a]pyrido[3,2-e]pyrimidin-5-ones. The cyclization of 2-(cinnamylamino)pyrido[2,3-d]pyrimidin-4(3H)-one under analogous conditions afforded linearly fused 4-phenyl-1,2,3,4-tetrahydro-6H-pyrido[2,3-d]pyrimido[1,2-a]pyrimidin-6-one. 2-(Allylamino)pyrido[2,3-d]pyrimidin-4(3H)-one reacted with iodine yielding 9-(iodomethyl)-8,9-dihydroimidazo[1,2-a]pyrido[3,2-e]pyrimidin-5(7H)-one as the major product, 2-(propargylamino)pyrido[2,3-d]pyrimidin-4(3H)-one gave rise to iodine addition product to the triple bond, and angularly fused 9-iodo-10-phenyl-7,8,9,10-tetrahydro-5H-pyrido[3,2-e]pyrimido[1,2-a]pyrimidin-5-one was obtained from the 2-(cinnamylamino) derivative. Electrophilic cyclization of 2-(allylamino)- and 2-(cinnamylamino)pyrido[2,3-d]pyrimidin-4(3H)-ones by the action of phenylsulfanyl chloride led to the formation of angularly fused 9-(phenylsulfanylmethyl)-8,9-dihydroimidazo[1,2-a]pyrido[3,2-e]pyrimidin-5(7H)-one and 10-phenyl-9-phenylsulfanyl-7,8,9,10-tetrahydro-5H-pyrido[3,2-e]pyrimido[1,2-a]pyrimidin-5-one. Pleiades Publishing, Ltd., 2015 Vas'kevich R. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02660, Kiev, Ukraine aut Dyachenko I. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02660, Kiev, Ukraine aut Vas'kevich A. "Kyiv Polytechnic Institute” National Technical University of Ukraine, pr. Peremohy 37, 03056, Kiev, Ukraine aut Rusanov E. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02660, Kiev, Ukraine aut Vovk M. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02660, Kiev, Ukraine aut Russian Journal of Organic Chemistry Pleiades Publishing 51/4(2015-04-01), 556-565 1070-4280 51:4<556 2015 51 11178 https://doi.org/10.1134/S1070428015040168 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1134/S1070428015040168 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Vas'kevich R. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02660, Kiev, Ukraine aut NATIONALLICENCE 700 1- Dyachenko I. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02660, Kiev, Ukraine aut NATIONALLICENCE 700 1- Vas'kevich A. "Kyiv Polytechnic Institute” National Technical University of Ukraine, pr. Peremohy 37, 03056, Kiev, Ukraine aut NATIONALLICENCE 700 1- Rusanov E. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02660, Kiev, Ukraine aut NATIONALLICENCE 700 1- Vovk M. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02660, Kiev, Ukraine aut NATIONALLICENCE 773 0- Russian Journal of Organic Chemistry Pleiades Publishing 51/4(2015-04-01), 556-565 1070-4280 51:4<556 2015 51 11178