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Volumn , Issue 18, 2005, Pages 3085-3094

Efficient synthesis of 6-amino-substituted pyridin-2(1H)-ones using in situ generated propiolic acid chloride

Author keywords

Cyclizations; N,S acetals; Pyridin 2(1H) ones; Ring closure; Thioacetals

Indexed keywords

AMINO ACIDS; CHLORIDE MINERALS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 28344456112     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872217     Document Type: Article
Times cited : (23)

References (44)
  • 6
    • 28344447266 scopus 로고    scopus 로고
    • note
    • 2-cHex R′ = cPr) with propiolic acid methyl ester we isolated the regioisomeric compounds 3 and 3′ in 21% and 27% yield.
  • 9
    • 84984383496 scopus 로고
    • (b) Huang, Z.-T.; Shi, X. Chem. Ber. 1990, 123, 541. During the revision of our manuscript the aza-annulation of acyclic ketene-N,S-acetals 4 with itaconic anhydride yielding tetrahydro-2-pyridones was reported:
    • (1990) Chem. Ber. , vol.123 , pp. 541
    • Huang, Z.-T.1    Shi, X.2
  • 21
    • 0000944684 scopus 로고    scopus 로고
    • The methylation of 3-keto thioamides after their generation applying Lawesson's reagent has also been described: Nishio, T. Helv. Chim. Acta 1998, 81, 1207.
    • (1998) Helv. Chim. Acta , vol.81 , pp. 1207
    • Nishio, T.1
  • 22
    • 0343594734 scopus 로고
    • Similar results from the reaction with dimethyl but-2-ynedioate were reported: Aggarwal, V.; Ila, H.; Junjappa, H. Synthesis 1983, 147.
    • (1983) Synthesis , pp. 147
    • Aggarwal, V.1    Ila, H.2    Junjappa, H.3
  • 35
    • 0000408807 scopus 로고
    • Stille explored the application of several acrylic acid derivatives in the aza-annulation of β-enamino esters and ketones: (a) Barta, N. C.; Brode, A.; Stille, J. R. J. Am. Chem. Soc. 1994, 116, 6201.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 6201
    • Barta, N.C.1    Brode, A.2    Stille, J.R.3
  • 39
    • 0001654017 scopus 로고
    • The spontaneous inflammation during the isolation of propiolic acid chloride was attributed to trace amounts of monochloroacetylene formed during destination: Balfour, W. J.; Greig, C. C.; Visaisouk, S. J. Org. Chem. 1974, 39, 725.
    • (1974) J. Org. Chem. , vol.39 , pp. 725
    • Balfour, W.J.1    Greig, C.C.2    Visaisouk, S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.