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Volumn 50, Issue 10, 2009, Pages 1105-1109

An efficient synthetic route to substituted tetrahydropyrimidines by Cu(OTf)2-mediated nucleophilic ring-opening followed by the [4+2] cycloaddition of N-tosylazetidines with nitriles

Author keywords

1,3 Diamine; 4+2 cycloaddition; Azetidine; Cu(OTf)2; SN2; Tetrahydropyrimidine

Indexed keywords

2 ARYL N TOSYLAZETIDINE DERIVATIVE; AZETIDINE DERIVATIVE; COPPER; DIAMINE DERIVATIVE; NITRILE; PYRIMIDINE DERIVATIVE; TETRAHYDROPYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 58349085081     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.12.035     Document Type: Article
Times cited : (31)

References (38)
  • 26
    • 58349083825 scopus 로고    scopus 로고
    • Presented in 2nd J-NOST conference held in Jaipur, India during October 11-14, 2006.
    • Presented in 2nd J-NOST conference held in Jaipur, India during October 11-14, 2006.
  • 27
    • 58349102450 scopus 로고    scopus 로고
    • Part of the work is included in the Ph.D. thesis of Kalpataru Das (2007, IIT Kanpur, India).
    • Part of the work is included in the Ph.D. thesis of Kalpataru Das (2007, IIT Kanpur, India).
  • 28
    • 58349111091 scopus 로고    scopus 로고
    • note
    • 2 was found to be a better and more efficient catalyst to effect the reaction.
  • 29
    • 58349103259 scopus 로고    scopus 로고
    • note
    • 3) using ethyl acetate/petroleum ether to provide the corresponding tetrahydropyrimidine 2. In cases where higher boiling nitriles were used, a modified purification method was followed. The reaction mixture was directly charged on a deactivated basic alumina column followed by washing with petroleum ether to remove and recover excess nitriles. Pure compounds were obtained using ethyl acetate/petroleum ether as eluent.
  • 32
    • 58349101688 scopus 로고    scopus 로고
    • note
    • 3S (M+H), calcd 347.1429; found 347.1427.
  • 38
    • 33847618382 scopus 로고    scopus 로고
    • For the synthesis of cis-disubstituted azetidines 27a-b:
    • For the synthesis of cis-disubstituted azetidines 27a-b:. Ghorai M.K., Das K., and Kumar A. Tetrahedron Lett. 48 (2007) 2471-2475
    • (2007) Tetrahedron Lett. , vol.48 , pp. 2471-2475
    • Ghorai, M.K.1    Das, K.2    Kumar, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.