PROTON- AND IODINE-INDUCED CYCLIZATION OF 2-(PENT-4-EN-1-YL)QUINAZOLIN- 4(3<i>H</i>)-ONES: SYNTHESIS OF PYRROLO[2,1-<i>b</i>]QUINAZOLINONE AND PYRIDO[1,2-<i>a</i>]QUINAZOLINONE DERIVATIVES

Authors

  • Ruslan I. Vaskevych Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094 https://orcid.org/0000-0001-9266-7600
  • Alla I. Vaskevych Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094 https://orcid.org/0000-0003-0370-6626
  • Nataliia O. Savinchuk Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094 https://orcid.org/0000-0003-1115-1798
  • Maryna V. Stasevych Lviv Polytechnic National University, 12 Bandera St., Lviv 79013
  • Svitlana V. Shiskina Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094. State Scientific Institution ''Institute for Single Crystals'' National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072
  • Mykhailo V. Vovk Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094 https://orcid.org/0000-0003-1753-3535

Keywords:

2-(pent-4-en-1-yl)quinazolin-4(3H)-ones, pyrrolo(pyrido)quinazolinones, trifluoromethanesulfonic acid, annulations, iodocyclizations

Abstract

2-(Pent-4-en-1-yl)quinazolin-4(3H)-ones in CF3SO3H solution undergo preferential cyclization into 1-ethyl-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-ones via the intermediate rearrangement in the alkenyl moiety, while 9-methyl-6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-ones are minor products. Iodocyclization of 2-(pent-4-en-1-yl)quinazolin-4(3H)-ones proceeds according to the 6-exo-trig cyclization mode to form 1-(iodomethyl)-1,2,3,4-tetrahydro-6H-pyrido[1,2-a]quinazolin-6-ones, which are further converted to their hexahydro derivatives by the diastereoselective reduction with NaBH4.

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Published

2024-12-13

Issue

Vol. 60 No. 9/10 (2024)

Section

Original Papers