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Volumn 60, Issue 31, 2004, Pages 6649-6655

A selective reductive amination of aldehydes by the use of Hantzsch dihydropyridines as reductant

Author keywords

Aldehyde; Direct reductive amination; Hantzsch dihydropyridine; Imine; Ketone; Lewis acid; Scandium (III) triflate

Indexed keywords

ALDEHYDE DERIVATIVE; AMINE; BENZYL DERIVATIVE; DIHYDROPYRIDINE DERIVATIVE; KETONE DERIVATIVE; REDUCING AGENT; TRIFLUOROMETHANESULFONIC ACID;

EID: 4143066159     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.096     Document Type: Article
Times cited : (104)

References (38)
  • 2
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    • and references cited therein
    • Lane C.F. Synthesis. 1975;135. and references cited therein
    • (1975) Synthesis , pp. 135
    • Lane, C.F.1
  • 28
    • 4143140664 scopus 로고    scopus 로고
    • Several Hantzsch dihydropyridine derivatives were synthesized and applied to the reaction. Other 4,4-dihydro derivatives afforded the reduction products, but the yields were slightly lower than that of 1a. 4-Substituted (alkyl or aryl) Hantzsch dihydropyridines did not react under the conditions
  • 29
    • 0002121370 scopus 로고
    • For a reference of the reduction by organic dihydro derivatives, see: B.M. Trost, Fleming I. Oxford: Pergamon
    • For a reference of the reduction by organic dihydro derivatives, see: Kellog R.M. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 8:1991;79 Pergamon, Oxford
    • (1991) Comprehensive Organic Synthesis , vol.8 , pp. 79
    • Kellog, R.M.1
  • 30
    • 33947290993 scopus 로고
    • 4, and so on, 5 Å sieves afforded the best results. See:
    • 4, and so on, 5 Å sieves afforded the best results. See: Westheimer F.H., Taguchi K. J. Org. Chem. 36:1971;1570
    • (1971) J. Org. Chem. , vol.36 , pp. 1570
    • Westheimer, F.H.1    Taguchi, K.2
  • 31
    • 4143103376 scopus 로고    scopus 로고
    • 3 in the reaction of entry 1, the yield were 34 and 5%, respectively
    • 3 in the reaction of entry 1, the yield were 34 and 5%, respectively
  • 32
    • 4143104463 scopus 로고    scopus 로고
    • 3
    • 3
  • 33
    • 4143074531 scopus 로고    scopus 로고
    • 3CN shows the selectivity between two substrates
    • 3CN shows the selectivity between two substrates
  • 34
    • 4143052237 scopus 로고    scopus 로고
    • note
    • 8. The results suggested that the participation of Lewis acid is crucial for the reaction progress, and that the iminium ion, which would be obtained via formation of the imine, did not play an important role in the reaction
  • 35
    • 4143116516 scopus 로고    scopus 로고
    • 3CN (0.4 mmol) in methanol, only 0.078 mmol (39%) of N,N′-dibenzyl derivative was obtained along with 0.16 mmol of benzyl alcohol
    • 3CN (0.4 mmol) in methanol, only 0.078 mmol (39%) of N,N′-dibenzyl derivative was obtained along with 0.16 mmol of benzyl alcohol
  • 36
    • 0345761268 scopus 로고    scopus 로고
    • The by-products included 2-phenyl- and 1-benzyl-2-phenylbenzimidazoles. In the presence of molecular oxygen, the yields of these compounds increased, and the results were applied to the synthesis of 2-arylbenzimidazole derivatives; see:
    • The by-products included 2-phenyl- and 1-benzyl-2-phenylbenzimidazoles. In the presence of molecular oxygen, the yields of these compounds increased, and the results were applied to the synthesis of 2-arylbenzimidazole derivatives; see: Nagata K., Itoh T., Ishikawa H., Ohsawa A. Heterocycles. 61:2003;93
    • (2003) Heterocycles , vol.61 , pp. 93
    • Nagata, K.1    Itoh, T.2    Ishikawa, H.3    Ohsawa, A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.