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Volumn 59, Issue 33, 2003, Pages 6363-6373

Practical synthesis of a highly functionalized thiazole ketone

Author keywords

Anion; Demethylation; Difluoromethylation; Reaction; Thiazole ketone

Indexed keywords

ANION; KETONE DERIVATIVE; NITRILE; THIAZOLE; THIAZOLE KETONE; UNCLASSIFIED DRUG;

EID: 0041703222     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00878-0     Document Type: Article
Times cited : (33)

References (62)
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    • Wallace, D.J.1    Chen, C.2
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    • Following a recent procedure from the literature (a). using vinyl acetate and Ir catalysis, we obtained low yields of vinyl ether 4 and significant amounts of the acetate byproduct
    • Following a recent procedure from the literature (a) Okimoto Y., Sakaguchi S., Ishii Y. J. Am. Chem. Soc. 124:(8):2002;1590-1591. using vinyl acetate and Ir catalysis, we obtained low yields of vinyl ether 4 and significant amounts of the acetate byproduct.
    • (2002) J. Am. Chem. Soc. , vol.124 , Issue.8 , pp. 1590-1591
    • Okimoto, Y.1    Sakaguchi, S.2    Ishii, Y.3
  • 11
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    • note
    • 4: C 66.66; H 4.97; N 8.64. Found C 66.37; H 4.88; N 8.57.
  • 12
    • 85031134846 scopus 로고    scopus 로고
    • 2OTs charge to 1.2 equiv. required an overnight age for the reaction to reach completion
    • 2OTs charge to 1.2 equiv. required an overnight age for the reaction to reach completion.
  • 15
    • 85031130429 scopus 로고    scopus 로고
    • NaOMe in DMF or MeCN was also effective for this reaction, but NaOtBu in THF was slow, even at 65°C
    • NaOMe in DMF or MeCN was also effective for this reaction, but NaOtBu in THF was slow, even at 65°C.
  • 16
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    • See the previous reference. Also: (a) Furukawa J., Kawabata N., Nishimura N. Tetrahedron Lett. 1966;3353 (b) Furukawa J., Kawabata N., Nishimura N. Tetrahedron. 27:1971;1799 (c) Furukawa J., Kawabata N. Adv. Organomet. Chem. 12:1974;83.
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    • See the previous reference. Also: (a) Furukawa J., Kawabata N., Nishimura N. Tetrahedron Lett. 1966;3353 (b) Furukawa J., Kawabata N., Nishimura N. Tetrahedron. 27:1971;1799 (c) Furukawa J., Kawabata N. Adv. Organomet. Chem. 12:1974;83.
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    • Furukawa, J.1    Kawabata, N.2    Nishimura, N.3
  • 21
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    • See the previous reference. Also: (a)
    • See the previous reference. Also: (a) Furukawa J., Kawabata N., Nishimura N. Tetrahedron Lett. 1966;3353 (b) Furukawa J., Kawabata N., Nishimura N. Tetrahedron. 27:1971;1799 (c) Furukawa J., Kawabata N. Adv. Organomet. Chem. 12:1974;83.
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    • Furukawa, J.1    Kawabata, N.2
  • 23
    • 85031141339 scopus 로고    scopus 로고
    • note
    • 3: C 68.74; H 6.29. Found C 68.58; H 6.09.
  • 24
    • 85031134939 scopus 로고    scopus 로고
    • The solid contained 5% aldehyde 7
    • The solid contained 5% aldehyde 7.
  • 25
    • 85031139860 scopus 로고    scopus 로고
    • 1-Methyl-2-pyrrolidinone and dimethylacetamide were also acceptable solvents for this reaction
    • 1-Methyl-2-pyrrolidinone and dimethylacetamide were also acceptable solvents for this reaction.
  • 31
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    • It has also been reported that methanesulfonic acid/methionine can facilitate demethylation in a similar manner without the stench of EtSNa. See: (a) Andre J.-D., Dormoy J.-R., Heymes A. Synth. Commun. 22:(16):1992;2313-2327 (b) Berenyi S., Csutoras C., Gyulai S., Rusznyak G. Synth. Commun. 31:(13):2001;1987-1992.
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    • Andre, J.-D.1    Dormoy, J.-R.2    Heymes, A.3
  • 32
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    • It has also been reported that methanesulfonic acid/methionine can facilitate demethylation in a similar manner without the stench of EtSNa. See: (a)
    • It has also been reported that methanesulfonic acid/methionine can facilitate demethylation in a similar manner without the stench of EtSNa. See: (a) Andre J.-D., Dormoy J.-R., Heymes A. Synth. Commun. 22:(16):1992;2313-2327 (b) Berenyi S., Csutoras C., Gyulai S., Rusznyak G. Synth. Commun. 31:(13):2001;1987-1992.
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    • Berenyi, S.1    Csutoras, C.2    Gyulai, S.3    Rusznyak, G.4
  • 34
    • 85031144619 scopus 로고    scopus 로고
    • All starting materials and products are commercially available
    • All starting materials and products are commercially available.
  • 35
    • 85031135296 scopus 로고    scopus 로고
    • For a general procedure, see Section 3 preparation of 8.
    • For a general procedure, see Section 3 preparation of 8.
  • 41
    • 85031140377 scopus 로고    scopus 로고
    • note
    • Attempts to difluoromethylate by direct addition of reagents to the crude demethylation reaction mixture resulted in low conversion of the phenol 8 to compound 9.
  • 42
    • 85031132316 scopus 로고    scopus 로고
    • note
    • 2Na) did not generate any of the dimer.
  • 44
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    • Recent variations: (a) Lin Y., Seifert C.M., Kang S.M., Dusza J.P., Lang S.A. Jr. J. Herterocycl. Chem. 16:1979;1377 (b) Knoll A., Liebscher J., Radeglia R. J. Prakt. Chem. 3:1985;463 (c) Romero-Ortega M., Aviles A., Cruz R., Fuentes A., Gomez R.M., Plata A. J. Org. Chem. 65:2000;7244 (d) Rajappa S., Sudarsanam V., Advani B.G., Rane A.V. Proc. Indian Acad. Sci. 91:1982;445.
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  • 45
    • 0018627083 scopus 로고
    • Recent variations: (a) Lin Y., Seifert C.M., Kang S.M., Dusza J.P., Lang S.A. Jr. J. Herterocycl. Chem. 16:1979;1377 (b) Knoll A., Liebscher J., Radeglia R. J. Prakt. Chem. 3:1985;463 (c) Romero-Ortega M., Aviles A., Cruz R., Fuentes A., Gomez R.M., Plata A. J. Org. Chem. 65:2000;7244 (d) Rajappa S., Sudarsanam V., Advani B.G., Rane A.V. Proc. Indian Acad. Sci. 91:1982;445.
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  • 46
    • 0034693341 scopus 로고    scopus 로고
    • Recent variations: (a) Lin Y., Seifert C.M., Kang S.M., Dusza J.P., Lang S.A. Jr. J. Herterocycl. Chem. 16:1979;1377 (b) Knoll A., Liebscher J., Radeglia R. J. Prakt. Chem. 3:1985;463 (c) Romero-Ortega M., Aviles A., Cruz R., Fuentes A., Gomez R.M., Plata A. J. Org. Chem. 65:2000;7244 (d) Rajappa S., Sudarsanam V., Advani B.G., Rane A.V. Proc. Indian Acad. Sci. 91:1982;445.
    • (2000) J. Org. Chem. , vol.65 , pp. 7244
    • Romero-Ortega, M.1    Aviles, A.2    Cruz, R.3    Fuentes, A.4    Gomez, R.M.5    Plata, A.6
  • 47
    • 0011447812 scopus 로고
    • Recent variations: (a)
    • Recent variations: (a) Lin Y., Seifert C.M., Kang S.M., Dusza J.P., Lang S.A. Jr. J. Herterocycl. Chem. 16:1979;1377 (b) Knoll A., Liebscher J., Radeglia R. J. Prakt. Chem. 3:1985;463 (c) Romero-Ortega M., Aviles A., Cruz R., Fuentes A., Gomez R.M., Plata A. J. Org. Chem. 65:2000;7244 (d) Rajappa S., Sudarsanam V., Advani B.G., Rane A.V. Proc. Indian Acad. Sci. 91:1982;445.
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    • Rajappa, S.1    Sudarsanam, V.2    Advani, B.G.3    Rane, A.V.4
  • 49
    • 85031142349 scopus 로고    scopus 로고
    • A similar reaction was carried out with excess PhCN and 1 equiv. of the TBS thiazole anion. The product was obtained in 88% yield
    • A similar reaction was carried out with excess PhCN and 1 equiv. of the TBS thiazole anion. The product was obtained in 88% yield.
  • 50
    • 85031138856 scopus 로고    scopus 로고
    • 15NOSSi (M+) m/z 262.0722, found m/z 262.0735
    • 15NOSSi (M+) m/z 262.0722, found m/z 262.0735.
  • 55
    • 85031132970 scopus 로고    scopus 로고
    • Available from Lancaster Synthesis
    • Available from Lancaster Synthesis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.