Indolizines and pyrrolo[1,2- c ]pyrimidines decorated with a pyrimidine and a pyridine unit respectively

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dc.contributor.authorPopa, Marcel Mirel
dc.contributor.authorGeorgescu, Emilian
dc.contributor.authorCaira, Mino R
dc.contributor.authorGeorgescu, Florentina
dc.contributor.authorDraghici, Constantin
dc.contributor.authorStan, Raluca
dc.contributor.authorDeleanu, Calin
dc.contributor.authorDumitrascu, Florea
dc.date.accessioned2021-10-08T06:20:12Z
dc.date.available2021-10-08T06:20:12Z
dc.date.issued2015
dc.description.abstractThe three possible structural isomers of 4-(pyridyl)pyrimidine were employed for the synthesis of new pyrrolo[1,2-c]pyrimidines and new indolizines, by 1,3-dipolar cycloaddition reaction of their corresponding N-ylides generated in situ from their corresponding cycloimmonium bromides. In the case of 4-(3-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine the quaternization reactions occur as expected at the pyridine nitrogen atom leading to pyridinium bromides and consequently to new indolizines via the corresponding pyridinium N-ylides. However, in the case of 4-(2-pyridyl)pyrimidine the steric hindrance directs the reaction to the pyrimidinium N-ylides and, subsequently, to the formation of the pyrrolo[1,2-c]pyrimidines. The new pyrrolo[1,2-c]pyrimidines and the new indolizines were structurally characterized through NMR spectroscopy. The X-ray structures of two of the starting materials, 4-(2-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine, are also reported.
dc.identifier.apacitationPopa, M. M., Georgescu, E., Caira, M. R., Georgescu, F., Draghici, C., Stan, R., ... Dumitrascu, F. (2015). Indolizines and pyrrolo[1,2- c ]pyrimidines decorated with a pyrimidine and a pyridine unit respectively. <i>Beilstein Journal of Organic Chemistry</i>, 11(4), 1079 - 1088. http://hdl.handle.net/11427/34224en_ZA
dc.identifier.chicagocitationPopa, Marcel Mirel, Emilian Georgescu, Mino R Caira, Florentina Georgescu, Constantin Draghici, Raluca Stan, Calin Deleanu, and Florea Dumitrascu "Indolizines and pyrrolo[1,2- c ]pyrimidines decorated with a pyrimidine and a pyridine unit respectively." <i>Beilstein Journal of Organic Chemistry</i> 11, 4. (2015): 1079 - 1088. http://hdl.handle.net/11427/34224en_ZA
dc.identifier.citationPopa, M.M., Georgescu, E., Caira, M.R., Georgescu, F., Draghici, C., Stan, R., Deleanu, C. & Dumitrascu, F. et al. 2015. Indolizines and pyrrolo[1,2- c ]pyrimidines decorated with a pyrimidine and a pyridine unit respectively. <i>Beilstein Journal of Organic Chemistry.</i> 11(4):1079 - 1088. http://hdl.handle.net/11427/34224en_ZA
dc.identifier.issn1860-5397
dc.identifier.issn2195-951X
dc.identifier.ris TY - Journal Article AU - Popa, Marcel Mirel AU - Georgescu, Emilian AU - Caira, Mino R AU - Georgescu, Florentina AU - Draghici, Constantin AU - Stan, Raluca AU - Deleanu, Calin AU - Dumitrascu, Florea AB - The three possible structural isomers of 4-(pyridyl)pyrimidine were employed for the synthesis of new pyrrolo[1,2-c]pyrimidines and new indolizines, by 1,3-dipolar cycloaddition reaction of their corresponding N-ylides generated in situ from their corresponding cycloimmonium bromides. In the case of 4-(3-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine the quaternization reactions occur as expected at the pyridine nitrogen atom leading to pyridinium bromides and consequently to new indolizines via the corresponding pyridinium N-ylides. However, in the case of 4-(2-pyridyl)pyrimidine the steric hindrance directs the reaction to the pyrimidinium N-ylides and, subsequently, to the formation of the pyrrolo[1,2-c]pyrimidines. The new pyrrolo[1,2-c]pyrimidines and the new indolizines were structurally characterized through NMR spectroscopy. The X-ray structures of two of the starting materials, 4-(2-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine, are also reported. DA - 2015 DB - OpenUCT DP - University of Cape Town IS - 4 J1 - Beilstein Journal of Organic Chemistry LK - https://open.uct.ac.za PY - 2015 SM - 1860-5397 SM - 2195-951X T1 - Indolizines and pyrrolo[1,2- c ]pyrimidines decorated with a pyrimidine and a pyridine unit respectively TI - Indolizines and pyrrolo[1,2- c ]pyrimidines decorated with a pyrimidine and a pyridine unit respectively UR - http://hdl.handle.net/11427/34224 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/34224
dc.identifier.vancouvercitationPopa MM, Georgescu E, Caira MR, Georgescu F, Draghici C, Stan R, et al. Indolizines and pyrrolo[1,2- c ]pyrimidines decorated with a pyrimidine and a pyridine unit respectively. Beilstein Journal of Organic Chemistry. 2015;11(4):1079 - 1088. http://hdl.handle.net/11427/34224.en_ZA
dc.language.isoeng
dc.publisher.departmentDepartment of Chemistry
dc.publisher.facultyFaculty of Science
dc.sourceBeilstein Journal of Organic Chemistry
dc.source.journalissue4
dc.source.journalvolume11
dc.source.pagination1079 - 1088
dc.source.urihttps://dx.doi.org/10.3762/bjoc.11.121
dc.subject.otherindolizine
dc.subject.othernitrogen heterocycles
dc.subject.other-ylide
dc.subject.other4-pyridylpyrimidine
dc.subject.otherpyrrolo[1
dc.subject.other2-
dc.subject.other]pyrimidine
dc.titleIndolizines and pyrrolo[1,2- c ]pyrimidines decorated with a pyrimidine and a pyridine unit respectively
dc.typeJournal Article
uct.type.publicationResearch
uct.type.resourceJournal Article
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