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Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones
- Source :
- Beilstein Journal of Organic Chemistry, Vol 12, Iss 1, Pp 301-308 (2016), Beilstein Journal of Organic Chemistry
- Publication Year :
- 2016
- Publisher :
- Beilstein Institut, 2016.
-
Abstract
- An oxidative reaction for the synthesis of 4-alkyl-substituted dihydroisoquinolin-1(2H)-ones with N-allylbenzamide derivatives as starting materials has been developed. The radical alkylarylation reaction proceeds through a sequence of alkylation and intramolecular cyclization. The substituent on the C–C double bond was found to play a key role for the progress of the reaction to give the expected products with good chemical yields. Additionally, N-methacryloylbenzamides were also suitable substrates for the current reaction and provided the alkyl-substituted isoquinoline-1,3(2H,4H)-diones in good yield.
- Subjects :
- N-allylbenzamides
cyclization
Double bond
oxidation
Substituent
Alkylation
010402 general chemistry
01 natural sciences
Medicinal chemistry
Full Research Paper
lcsh:QD241-441
chemistry.chemical_compound
dihydroisoquinolin-1(2H)-one
lcsh:Organic chemistry
Isoquinoline
lcsh:Science
chemistry.chemical_classification
010405 organic chemistry
Organic Chemistry
Intramolecular cyclization
C(sp3)–H bond functionalization
0104 chemical sciences
Chemistry
chemistry
Cascade
Yield (chemistry)
lcsh:Q
Subjects
Details
- ISSN :
- 18605397
- Volume :
- 12
- Database :
- OpenAIRE
- Journal :
- Beilstein Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....b5181fb49d2512259765c4e9c5635913