About: Three-Component (Domino) Reaction Affording Substituted Pyrroloquinazolines: Cyclization Regioselectivity and Stereoselectivity

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About: Three-Component (Domino) Reaction Affording Substituted Pyrroloquinazolines: Cyclization Regioselectivity and Stereoselectivity Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	The cyclization involving 2-(aminomethyl)aniline, methyl 3,3,3-trifluoropyruvate, and various oxo compound afforded linearly annulated pyrroloquinazolines, for example, (2R,3aS)-2-hydroxy-3a-phenyl-2-trifluoromethyl-3,3a, 4,9-tetrahydropyrrolo[2,1-b]quinazolin-1(2H)-one (cis-8), as the major product, possessing the skeleton of the alkaloids of the vasicine group, along with angularly annulated products, for example, (2S,3aR)-2-hydroxy-3a-phenyl-2-trifluorometh-yl-3,3a,4,5-tetrahydropyrrolo[1,2-a]quinazolin-1(2H)-one (cis-18). The effects of the nature of the oxo compound and the temperature on the ratio of the linear and angular cyclization products, as well as the diastereoselectivity of the product formation, were studied, with an increase in temperature leading to improved selectivity. Some of the linear pyrroloquinazolines were stereoselectively didehydrogenated at the quinazoline ring by the trifluoropyruvate. The cyclization involving 2-(aminomethyl)aniline, methyl 3,3,3-trifluoropyruvate, and various oxo compound afforded linearly annulated pyrroloquinazolines, for example, (2R,3aS)-2-hydroxy-3a-phenyl-2-trifluoromethyl-3,3a, 4,9-tetrahydropyrrolo[2,1-b]quinazolin-1(2H)-one (cis-8), as the major product, possessing the skeleton of the alkaloids of the vasicine group, along with angularly annulated products, for example, (2S,3aR)-2-hydroxy-3a-phenyl-2-trifluorometh-yl-3,3a,4,5-tetrahydropyrrolo[1,2-a]quinazolin-1(2H)-one (cis-18). The effects of the nature of the oxo compound and the temperature on the ratio of the linear and angular cyclization products, as well as the diastereoselectivity of the product formation, were studied, with an increase in temperature leading to improved selectivity. Some of the linear pyrroloquinazolines were stereoselectively didehydrogenated at the quinazoline ring by the trifluoropyruvate. (en)
Title	Three-Component (Domino) Reaction Affording Substituted Pyrroloquinazolines: Cyclization Regioselectivity and Stereoselectivity Three-Component (Domino) Reaction Affording Substituted Pyrroloquinazolines: Cyclization Regioselectivity and Stereoselectivity (en)
skos:prefLabel	Three-Component (Domino) Reaction Affording Substituted Pyrroloquinazolines: Cyclization Regioselectivity and Stereoselectivity Three-Component (Domino) Reaction Affording Substituted Pyrroloquinazolines: Cyclization Regioselectivity and Stereoselectivity (en)
skos:notation	RIV/60461373:22310/13:43895076!RIV14-MSM-22310___
http://linked.open...avai/riv/aktivita	Z
http://linked.open...avai/riv/aktivity	Z(MSM6046137301), Z(MSM6046137307)
http://linked.open...iv/cisloPeriodika	7
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Paleček, Jiří Kvíčala, Jaroslav
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	Vysoká škola chemicko-technologická v Praze / Fakulta chemické technologie
http://linked.open...dnocenehoVysledku	111034
http://linked.open...ai/riv/idVysledku	RIV/60461373:22310/13:43895076
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Dehydrogenation; Polycycles; Nitrogen heterocycles; Multicomponent reactions; Cyclization (en)
http://linked.open.../riv/klicoveSlovo	Multicomponent reactions Polycycles Dehydrogenation Nitrogen heterocycles Cyclization
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[E71E64EFC97E]
http://linked.open...i/riv/nazevZdroje	European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	2 (xsd:int)
http://linked.open...cetTvurcuVysledku	4 (xsd:int)
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	MAR 2013
http://linked.open...iv/tvurceVysledku	Kvíčala, Jaroslav Paleček, Jiří Dolenský, Bohumil Paleta, Oldřich
http://linked.open...ain/vavai/riv/wos	000316196500011
http://linked.open...n/vavai/riv/zamer	Catalytic processes in chemistry and chemical technology Physico-chemical methods of analysis and characterization of chemical systems and biosystems
issn	1434-193X
number of pages	9 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/ejoc.201201356
http://localhost/t...ganizacniJednotka	22310

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