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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22340%2F13%3A43895076" target="_blank" >RIV/60461373:22340/13:43895076 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22310/13:43895076 RIV/60461373:22810/13:43895076

Výsledek na webu

<a href="http://dx.doi.org/10.1002/ejoc.201201356" target="_blank" >http://dx.doi.org/10.1002/ejoc.201201356</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/ejoc.201201356" target="_blank" >10.1002/ejoc.201201356</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

—

Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2013

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

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Svazek periodika

MAR 2013

Číslo periodika v rámci svazku

7

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

9

Strana od-do

1262-1270

Kód UT WoS článku

000316196500011

EID výsledku v databázi Scopus

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