About: The unambiguous synthesis and NMR assignment of 4-alkoxy and 3-alkylquinazolines

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About: The unambiguous synthesis and NMR assignment of 4-alkoxy and 3-alkylquinazolines Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://www.sciencedirect.com/science/article/pii/S004040201201873X
Description	Contrary to a number of reports, alkylations of the privileged 3,4-dihydroquinazoline scaffold provide N3-alkylated products, and not 4-alkoxyquinazolines. To correctly assign the structure, C-13 NMR shifts of the -Z-CHn- (Z=O, N) fragment are necessary; resonances in the 45-55 ppm range are indicative of N3-allcylation. Treatment of 3,4-dihydroquinazoline-4-one with p-TsCl afforded the N3-tosylated compound, whose reaction with an amine yielded the corresponding N3-alkyl derivative. A mechanism corroborated by N-15-labeling involving pyrimidine ring opening and recyclisation is proposed. Finally, the unambiguous preparation of 4-alkoxyquinazolines is described via treatment of 3,4-dihydroquinazoline-4-ones with PCl5 followed by an alkoxide. Contrary to a number of reports, alkylations of the privileged 3,4-dihydroquinazoline scaffold provide N3-alkylated products, and not 4-alkoxyquinazolines. To correctly assign the structure, C-13 NMR shifts of the -Z-CHn- (Z=O, N) fragment are necessary; resonances in the 45-55 ppm range are indicative of N3-allcylation. Treatment of 3,4-dihydroquinazoline-4-one with p-TsCl afforded the N3-tosylated compound, whose reaction with an amine yielded the corresponding N3-alkyl derivative. A mechanism corroborated by N-15-labeling involving pyrimidine ring opening and recyclisation is proposed. Finally, the unambiguous preparation of 4-alkoxyquinazolines is described via treatment of 3,4-dihydroquinazoline-4-ones with PCl5 followed by an alkoxide. (en)
Title	The unambiguous synthesis and NMR assignment of 4-alkoxy and 3-alkylquinazolines The unambiguous synthesis and NMR assignment of 4-alkoxy and 3-alkylquinazolines (en)
skos:prefLabel	The unambiguous synthesis and NMR assignment of 4-alkoxy and 3-alkylquinazolines The unambiguous synthesis and NMR assignment of 4-alkoxy and 3-alkylquinazolines (en)
skos:notation	RIV/00216208:11160/13:10145815!RIV14-GA0-11160___
http://linked.open...avai/predkladatel	Farmaceutická fakulta v Hradci Králové
http://linked.open...avai/riv/aktivita	I P S
http://linked.open...avai/riv/aktivity	I, P(GAP207/10/2048), S
http://linked.open...iv/cisloPeriodika	6
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Suchánková, Jana Palát, Karel Kuneš, Jiří Novák, Zdeněk Pour, Milan Špulák, Marcel
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Karlova v Praze / Farmaceutická fakulta v Hradci Králové
http://linked.open...dnocenehoVysledku	112535
http://linked.open...ai/riv/idVysledku	RIV/00216208:11160/13:10145815
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	N3-alkylation; O-alkylation; NMR; Quinazoline (en)
http://linked.open.../riv/klicoveSlovo	NMR N3-alkylation O-alkylation Quinazoline
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[634F7CE1FA49]
http://linked.open...i/riv/nazevZdroje	Tetrahedron
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	6 (xsd:int)
http://linked.open...cetTvurcuVysledku	6 (xsd:int)
http://linked.open...vavai/riv/projekt	Chiral Quinazoline Alkaloids: Potential Prototypes of Novel Antiasthmatics and Organocatalysts
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	69
http://linked.open...iv/tvurceVysledku	Kuneš, Jiří Palát, Karel Novák, Zdeněk Pour, Milan Špulák, Marcel Pourová, Jana
http://linked.open...ain/vavai/riv/wos	000315613000004
issn	0040-4020
number of pages	7 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.tet.2012.12.031
http://localhost/t...ganizacniJednotka	11160

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