Reaction of Malonates with Camphoranile. Synthesis of 4-Hydroxy-2-pyridones attached to the Bornane Ring System

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F06%3A63504704" target="_blank" >RIV/70883521:28110/06:63504704 - isvavai.cz</a>

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Reaction of Malonates with Camphoranile. Synthesis of 4-Hydroxy-2-pyridones attached to the Bornane Ring System

Original language description

The reaction of camphoranils N-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)benzenamine and N-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)benzenamine with magic malonates (bis(2,4,6-trichlorophenyl) 2-butyl- and 2-phenylmalonates) leads to 4-hydroxy-2(1H)-pyridones attached to bornane ring system (e.g. (5S,8R)-3-butyl-5,6,7,8-tetrahydro-4-hydroxy-8,9,9-trimethyl-1-phenyl-5,8-methanoquinolin-2(1H)-one) in good yields. Less satisfactory yields were obtained with the di-Et 2-phenylmalonate. The reaction of an excess of di-Et malonate with N-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)benzenamine yields the pyrono deriv. 4-hydroxy-7,11,11-trimethyl-6-phenyl-7,8,9,10-tetrahydro-7,10-methano-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione, which canreadily be degraded via the acetyl deriv. 3-acetyl-4-hydroxy-8,9,9-trimethyl-1-phenyl-5,6,7,8-tetrahydro-5,8-methanoquinolin-2(1H)-one to the basic structure 4-hydroxy-8,9,9-trimethyl-1-phenyl-5,6,7,8-tetrahydro-5,8-methanoquinolin-2(1H)-

Czech name

Reakce malonátů s anily kafru. Syntéza 4-hydroxy-2-pyridonů připojených k bornanovému cyklickému systému

Czech description

Reakce anilů kafru, N-((1R,4R)-1,7,7-trimethylbicyklo[2.2.1]heptan-2-yliden)benzenaminu a N-(1,7,7-trimethylbicyklo[2.2.1]heptan-2-yliden)benzenaminu, s magickými malonáty (bis(2,4,6-trichlorfenyl)-2-butyl- a bis(2,4,6-trichlorfenyl)-2-fenylmalonát) vedeke 4-hydroxy-2(1H)-pyridonům připojeným k bornanovému cyklickému systému (např. (5S,8R)-3-butyl-5,6,7,8-tetrahydro-4-hydroxy-8,9,9-trimethyl-1-fenyl-5,8-methanochinolin-2(1H)-on) s dobrými výtěžky. Méně uspokojivé výtěžky byly dosaženy s diethyl-2-fenylmalonátem. Reakce přebytku diethyl-malonátu s N-(1,7,7-trimethylbicyklo[2.2.1]heptan-2-yliden)benzenaminem poskytuje pyronoderivát 4-hydroxy-7,11,11-trimethyl-6-fenyl-7,8,9,10-tetrahydro-7,10-methano-2H-pyrano[3,2-c]chinolin-2,5(6H)-dion, který lze snadno odbourat přes jeho acetylderivát 3-acetyl-4-hydroxy-8,9,9-trimethyl-1-fenyl-5,6,7,8-tetrahydro-5,8-methanochinolin-2(1H)-on na základní sloučeninu se structurou 4-hydroxy-8,9,9-trimethyl-1-fenyl-5,6,7,8-tetrahydro-5,8-methanochinolin-2(

Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

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Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2006

Confidentiality

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

Name of the periodical

Journal of Heterocyclic Chemistry

ISSN

0022-152X

e-ISSN

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Volume of the periodical

43

Issue of the periodical within the volume

4

Country of publishing house

US - UNITED STATES

Number of pages

1

Pages from-to

1105-1109

UT code for WoS article

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EID of the result in the Scopus database

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