Three-Component (Domino) Reaction Affording Substituted Pyrroloquinazolines: Cyclization Regioselectivity and Stereoselectivity
The result's identifiers
Result code in 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>
Alternative codes found
RIV/60461373:22310/13:43895076 RIV/60461373:22810/13:43895076
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Three-Component (Domino) Reaction Affording Substituted Pyrroloquinazolines: Cyclization Regioselectivity and Stereoselectivity
Original language 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.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
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Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)
Others
Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
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Volume of the periodical
MAR 2013
Issue of the periodical within the volume
7
Country of publishing house
DE - GERMANY
Number of pages
9
Pages from-to
1262-1270
UT code for WoS article
000316196500011
EID of the result in the Scopus database
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