• Bulletin of the Korean Chemical Society
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• v.16 no.11
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• pp.1064-1067
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• 1995

A convenient method for the synthesis of N-substituted isoindolin-1-ones is disclosed in palladium(0)-catalyzed heterocyclization of o-bromobenzylbromide with carbon monoxide (CO) and primary amines in DMF at 100 ℃.

• Bulletin of the Korean Chemical Society
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• v.33 no.5
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• pp.1457-1464
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• 2012

An ecofriendly catalytic route for selective synthesis of $N$-substituted azacyclopentanes, nitrogen-containing heterocyclic intermediates for many bioactive compounds, was established by carrying out $N$-heterocyclization (di $N$-alkylation) of primary amines with 1,4-dichloro butane (as dialkylating agent) using catalytic amount of hydrotalcite as solid base catalyst. The hydrotalcite was found to be efficient solid base catalyst for di $N$-alkylation of different primary amines (aniline, benzyl amine, cyclohexyl amine and n-butyl amine) giving 82 to 96% conversion (at optimized reaction condition) of 1,4-dichloro butane and > 99% selectivity of respective $N$-substituted azacyclopentanes within 30 min. under solvent free condition. The reaction parameters significantly influence the conversion of 1,4-dichloro butane to $N$-substituted azacyclopentanes. The nature of substituent present on amino group affects the reactivity of amine substrates for di $N$-alkylation reaction with 1,4-dichloro butane. The 1,4-dichloro butane was found to be highly reactive alkylating agent for di $N$-alkylation of amines as compared to 1,4-dihydroxy butane. The reusability of the catalyst and its chemical stability in the reaction was demonstrated.

• Bulletin of the Korean Chemical Society
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• v.34 no.11
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• pp.3467-3470
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• 2013