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Volumn , Issue 18, 2007, Pages 2809-2814

Unprecedented reaction between ethyl α-cyanocinnamate and o-phenylenediamine: Development of an efficient method for the transfer hydrogenation of electronically depleted olefins

Author keywords

Benzimidazoline; Electronically depleted olefins; Hydrogen transfer; Metal free reduction; Organocatalytic reaction

Indexed keywords

ALKENE DERIVATIVE; CINNAMIC ACID DERIVATIVE; PHENYLENEDIAMINE;

EID: 36549007397     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-991087     Document Type: Article
Times cited : (20)

References (26)
  • 26
    • 36549069972 scopus 로고    scopus 로고
    • General Procedure for Transfer Hydrogenation of Deactivated Olefins Two-Component Reaction In an open vial, ethyl α-cyanocinnamate (1a, 2.0 mmol)and o-phenylenediamine (2, 1.0 mmol) were mixed thoroughly and heated in an oil bath at 100°C. The reaction mixture liquefied and resolidified within half an hour and the reaction was found to be complete (TLC, After cooling the resultant semi-solid reaction mixture, a 7:3 mixture of EtOAc and PE (15 mL) was added and the insoluble 2- phenylbenzimidazole (4a) was filtered out (92% yield, The filtrate was concentrated, and after column chromatography of the residue using 5% EtOAc-PE as eluent, the reduced product 3a and ethyl cyanoacetate (5a) were isolated in 95% and 60% yield, respectively. Three-Component Reaction In an open vial, benzaldehyde, ethyl benzylidenecyanoacetate, and o-phenylenediamine (1:1:1, 1 mmol each) were mixed thoroughly and then heated in an oil ba
    • +].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.