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Volumn 25, Issue 5-6, 2006, Pages 465-473

Hydro-, halo- and seleno-carbamoylation of cyclic enol ethers and dihydropyridines: New mechanistic pathways for Passerini-and Ugi-type multicomponent reactions

Author keywords

Dihydropyridines; Enol ethers; Isonitriles; Multicomponent reactions

Indexed keywords

CHLORINE COMPOUNDS; CONDENSATION REACTIONS; ETHERS; REACTION INTERMEDIATES; REACTION KINETICS; SUBSTITUTION REACTIONS;

EID: 33745778655     PISSN: 1611020X     EISSN: 16110218     Source Type: Journal    
DOI: 10.1002/qsar.200540193     Document Type: Article
Times cited : (17)

References (33)
  • 1
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    • J. Zhu, H. Bienaymé (Eds.), Wiley-VCH, Weinheim
    • For an overview of MCRs, see: a) J. Zhu, H. Bienaymé (Eds.), Multicomponent Reactions, Wiley-VCH, Weinheim, 2005;
    • (2005) Multicomponent Reactions
  • 5
    • 85192675262 scopus 로고
    • I. Ugi, S. Lohberger, R. Karl, in: B. M. Trost, I. Fleming (Eds.), Pergamon Press, Oxford, chapter 4
    • a) I. Ugi, S. Lohberger, R. Karl, in: B. M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991, Vol. 2, chapter 4;
    • (1991) Comprehensive Organic Synthesis , vol.2
  • 10
    • 0036012737 scopus 로고    scopus 로고
    • The presence of an electron-withdrawing group at the β-position is needed for the stability of the compounds. For a recent review on the chemistry of dihydropyridines, see: R. Lavilla, J. Chem. Soc., Perkin Trans, 1 2002, 1141.
    • (2002) J. Chem. Soc., Perkin Trans, 1 , pp. 1141
    • Lavilla, R.1
  • 15
    • 0035898869 scopus 로고    scopus 로고
    • a) For a recent mechanistic study on the hydrolysis of isonitriles, see: K. Sung, C.-C. Chen, Tetrahedron Lett. 2001, 42, 4845.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 4845
    • Sung, K.1    Chen, C.-C.2
  • 17
    • 85192683226 scopus 로고    scopus 로고
    • note
    • When we used (+)-camphorsulfonic acid as the catalyst, we observed a very low enantiomeric excess (2%), as determined by chiral HPLC.
  • 18
    • 1842465553 scopus 로고
    • The interaction of acetals with isocyanides under acid catalysis has been reported. See: H. Pellissier, A. Meou, G. Gil, Tetrahedron Lett. 1986, 27, 2979.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 2979
    • Pellissier, H.1    Meou, A.2    Gil, G.3
  • 20
    • 2342429191 scopus 로고    scopus 로고
    • b) For a detailed account on this chemistry, see: R. Lavilla, Curr. Org. Chem. 2004, 8, 715.
    • (2004) Curr. Org. Chem. , vol.8 , pp. 715
    • Lavilla, R.1
  • 23
    • 85192685574 scopus 로고    scopus 로고
    • note
    • + addition, the ease of oxidation of the DHP, and also the kinetics of the isocyanide trapping.
  • 24
    • 85192676702 scopus 로고    scopus 로고
    • note
    • Traces of water in the reaction medium may account for the generation of HBr, which in turn may promote the hydrocarbamoylation process.
  • 26
    • 85192669700 scopus 로고    scopus 로고
    • note
    • This compound showed a single relative stereochemistry which was not determined. Presumably displaying the iodo and the carbamoyl substituents on opposite faces.
  • 28
    • 85192679330 scopus 로고    scopus 로고
    • J. Zhu, H. Bienaymé (Eds.), Wiley-VCH, Weinheim, chapter 2
    • For an excellent review on the subject, see: S. Marcaccini, T. Torroba, in: J. Zhu, H. Bienaymé (Eds.), Multicomponent Reactions, Wiley-VCH, Weinheim, 2005, chapter 2.
    • (2005) Multicomponent Reactions
    • Marcaccini, S.1    Torroba, T.2
  • 33
    • 85192674004 scopus 로고    scopus 로고
    • note
    • For instance, Zn-promoted radical additions of halo-tetrahydropyridines 5 upon electron-deficient olefins afforded the expected products.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.