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Volumn 44, Issue 5, 2007, Pages 1059-1064

(±)-2-Alkyl-1,2,3,4-tetrahydroquinoline-3-carboxylic esters by a catalyst and pressure dependent tandem reduction-reductive amination reaction

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4 TETRAHYDROQUINOLINE 3 CARBOXYLIC ESTER; 1,4 DIHYDROQUINOLINE DERIVATIVE; BETA KETO ESTER DERIVATIVE; CARBON; ESTER DERIVATIVE; PALLADIUM; QUINOLINE DERIVATIVE; TETRAHYDROQUINOLINE; UNCLASSIFIED DRUG;

EID: 36649012859     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570440513     Document Type: Article
Times cited : (11)

References (19)
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    • Others have also used reductive amination under hydrogenation conditions to prepare heterocyclic ring systems, see: [a] Stevens, R. V, Lee, A. W. M. J. Chem. Soc, Chem. Commun. 1982, 102 and 103
    • Others have also used reductive amination under hydrogenation conditions to prepare heterocyclic ring systems, see: [a] Stevens, R. V.; Lee, A. W. M. J. Chem. Soc., Chem. Commun. 1982, 102 and 103.
  • 7
    • 85036978704 scopus 로고    scopus 로고
    • the preceding paper in this issue. This article describes the synthesis of 1a-g along with cyclizations of more sterically congested β-keto esters
    • Bunce, R. A.; Schammerhorn, J. E. J. Heterocyclic Chem., the preceding paper in this issue. This article describes the synthesis of 1a-g along with cyclizations of more sterically congested β-keto esters.
    • J. Heterocyclic Chem
    • Bunce, R.A.1    Schammerhorn, J.E.2
  • 8
    • 36649028010 scopus 로고
    • US Patent 4656283, 134222
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    • (1987) Chem Abstr , vol.107
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  • 9
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    • All reactions yielded up to 10 mg of the N-methyl derivative of the major tetrahydroquinoline. This could arise from alkylation of the product by methanol solvent or from traces of formaldehyde in the commercial solvent. Alkylation of amines by alcohol solvents has been observed previously, but only with a nickel catalyst, see Adkins, H.; Cramer, H. R. J. Am. Chem. Soc. 1930, 52, 4349. Note: Catalysts showing this side reaction are all prepared under acidic conditions. Residual acid in these catalysts could facilitate this alkylation process.
    • All reactions yielded up to 10 mg of the N-methyl derivative of the major tetrahydroquinoline. This could arise from alkylation of the product by methanol solvent or from traces of formaldehyde in the commercial solvent. Alkylation of amines by alcohol solvents has been observed previously, but only with a nickel catalyst, see Adkins, H.; Cramer, H. R. J. Am. Chem. Soc. 1930, 52, 4349. Note: Catalysts showing this side reaction are all prepared under acidic conditions. Residual acid in these catalysts could facilitate this alkylation process.
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    • For diene substrates with the potential to aromatize, palladium catalysts have been previously observed to promote disproportionation while platinum catalysts were found to favor hydrogenation, see
    • For diene substrates with the potential to aromatize, palladium catalysts have been previously observed to promote disproportionation while platinum catalysts were found to favor hydrogenation, see Friedlin, L. K.; Polkovnikov, B. D.; Egorov, Y. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1959, 910;
    • (1959) Izv. Akad. Nauk SSSR, Ser. Khim , pp. 910
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    • The reaction also produced the tetrahydroquinoline products in comparable yields under 1 atmosphere of hydrogen
    • The reaction also produced the tetrahydroquinoline products in comparable yields under 1 atmosphere of hydrogen.


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