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Volumn 15, Issue 10, 2013, Pages 2713-2717

Selective autoxidation of benzylamines: Application to the synthesis of some nitrogen heterocycles

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EID: 84884613178     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c3gc41186a     Document Type: Article
Times cited : (108)

References (60)
  • 9
    • 33947489306 scopus 로고
    • For selected examples of oxidation of benzylamines to N-benzylbenzylideneimine using oxidizing agents other than molecular oxygen, see H2O2
    • R. W. Layer Chem. Rev. 1963 63 489
    • (1963) Chem. Rev. , vol.63 , pp. 489
    • Layer, R.W.1
  • 22
    • 84884623048 scopus 로고    scopus 로고
    • For examples of catalytic aerobic oxidation of benzylamines to N-benzylbenzaldimines, see: Cu/TEMPO
    • M. Largeron Eur. J. Org. Chem. 2013 5225
    • (2013) Eur. J. Org. Chem. , pp. 5225
    • Largeron, M.1
  • 48
    • 84871867838 scopus 로고    scopus 로고
    • For examples of autoxidation of amines, see
    • M. Largeron M. B. Fleury Science 2013 339 43
    • (2013) Science , vol.339 , pp. 43
    • Largeron, M.1    Fleury, M.B.2
  • 52
    • 84862560384 scopus 로고    scopus 로고
    • It should be noted that to maintain a constant oxygen pressure in the reactions using oxygen in air as an oxidant, continuous aeration is required, especially on a large scale. This aeration achieved by passing the air through the reaction or by performing the reaction in an open flask is not convenient and causes loss of volatile starting materials such as benzylamine
    • T. B. Nguyen J. Sorres M. Q. Tran L. Ermolenko A. Al-Mourabit Org. Lett. 2012 14 3202
    • (2012) Org. Lett. , vol.14 , pp. 3202
    • Nguyen, T.B.1    Sorres, J.2    Tran, M.Q.3    Ermolenko, L.4    Al-Mourabit, A.5
  • 53
    • 80052307522 scopus 로고    scopus 로고
    • The purification of imines by column chromatography was done rapidly with silica gel pretreated with NEt3 (see ESI) AcOH is used as a cyclizing catalyst in the transimination step + 1a → y + 2a and the cyclization step y → z in the scheme. Other catalysts tested (NH 4Cl, NH4OAc, HCl, BnNH2·HCl, etc.) are also as effective as AcOH. The aromatization step z → w occurs spontaneously at this temperature
    • L. Liu S. Zhang X. Fu C. Yan Chem. Commun. 2011 10148
    • (2011) Chem. Commun. , vol.10 , pp. 10148
    • Liu, L.1    Zhang, S.2    Fu, X.3    Yan, C.4
  • 54
    • 84884638412 scopus 로고
    • Part 1, 40, 331-390 (ed N. Preston), John Wiley & Sons, Inc. Hoboken, NJ, USA For some examples of using benzylamines in nitrogen heterocycle synthesis, see
    • D. M. Smith, Chem. Heterocycl. Compd., 1981, Part 1, 40, pp. 331-390 (ed P. N. Preston), John Wiley & Sons, Inc. Hoboken, NJ, USA
    • (1981) Chem. Heterocycl. Compd.
    • Smith, D.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.