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Volumn 45, Issue 44, 2004, Pages 8183-8185

Sequential Birch reduction-allylation and Cope rearrangement of o-anisic acid derivatives

Author keywords

3,3 Sigmatropic rearrangement; Birch reduction allylation; Cope rearrangement; Quaternary carbon synthesis

Indexed keywords

ANISIC ACID; CYCLOALKENE;

EID: 4744343496     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.09.025     Document Type: Article
Times cited : (8)

References (28)
  • 8
    • 0038695134 scopus 로고    scopus 로고
    • For reviews of the Cope rearrangement, see: U. Nubbemeyer Synthesis 7 2003 961
    • (2003) Synthesis , vol.7 , pp. 961
    • Nubbemeyer, U.1
  • 9
    • 0000746177 scopus 로고
    • Cope, Oxy-Cope and Anionic Oxy-Cope Rearrangements
    • B.M. Trost I. Fleming Pergamon Oxford
    • R.K. Hill Cope, Oxy-Cope and Anionic Oxy-Cope Rearrangements B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Oxford Chapter 7.1
    • (1991) Comprehensive Organic Synthesis , vol.5
    • Hill, R.K.1
  • 11
    • 0000729869 scopus 로고
    • One example involves cyclohexadienone rearrangement: B. Miller J. Am. Chem. Soc. 87 1965 5115
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 5115
    • Miller, B.1
  • 16
    • 0010291446 scopus 로고
    • Partial Reduction of Aromatic Rings by Dissolving Metals and by Other Methods
    • B.M. Trost I. Fleming Pergamon Oxford
    • L.N. Mander Partial Reduction of Aromatic Rings by Dissolving Metals and by Other Methods B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 8 1991 Pergamon Oxford Chapter 3.4
    • (1991) Comprehensive Organic Synthesis , vol.8
    • Mander, L.N.1
  • 17
    • 4744348736 scopus 로고    scopus 로고
    • N-Pyrrolidinyl 2-methoxybenzamide, 3, was synthesized from o-anisic acid by conversion to the acid chloride and reaction with pyrrolidine
    • The product matched the spectroscopic data previously reported
    • N-Pyrrolidinyl 2-methoxybenzamide, 3, was synthesized from o-anisic acid by conversion to the acid chloride and reaction with pyrrolidine. The product matched the spectroscopic data previously reported in: A.R. Katrizky, H.-Y. He, and K. Suzuki J. Org. Chem. 65 2000 8210
    • (2000) J. Org. Chem. , vol.65 , pp. 8210
    • Katrizky, A.R.1    He, H.-Y.2    Suzuki, K.3
  • 18
    • 4744349293 scopus 로고    scopus 로고
    • note
    • 7
  • 19
    • 4744367843 scopus 로고    scopus 로고
    • note
    • All new compounds were pure as determined by a combination of NMR, GC, and, where applicable, melting point. GC analyses were performed on an Agilent 6890 gas chromatograph with an EIMS detector fitted with a 30 m x 0.25 mm column filled with crosslinked 5% PH ME siloxane (0.25 μm film thickness); gas pressure: 7.63 psi He. The method for analysis of all samples involved heating from 50 to 150°C (10°C/min), then from 150 to 260°C (5°C/min) and finally holding at 260°C for 2 min
  • 20
    • 4744354388 scopus 로고    scopus 로고
    • note
    • 7
  • 21
    • 0041868170 scopus 로고    scopus 로고
    • N-Pyrrolidinyl 2-methoxy-5-methylbenzamide, 7, was synthesized from 5-methylsalicylate by dimethylation and saponification to make 2-methoxy-5-methyl-benzoic acid. Conversion of the acid to the acid chloride and reaction with pyrrolidine afforded 5
    • which matched the previously reported spectroscopic data
    • N-Pyrrolidinyl 2-methoxy-5-methylbenzamide, 7, was synthesized from 5-methylsalicylate by dimethylation and saponification to make 2-methoxy-5-methyl-benzoic acid. Conversion of the acid to the acid chloride and reaction with pyrrolidine afforded 5, which matched the previously reported spectroscopic data in: D.J. Hart, and F. Havas C. R. Acad. Sci., Ser. IIc: Chim. 4 2001 591
    • (2001) C. R. Acad. Sci., Ser. IIc: Chim. , vol.4 , pp. 591
    • Hart, D.J.1    Havas, F.2
  • 22
    • 4744375227 scopus 로고    scopus 로고
    • note
    • 7
  • 23
    • 4744361463 scopus 로고    scopus 로고
    • note
    • 7
  • 24
    • 0026692815 scopus 로고
    • For an example of conjugate addition to a similar 2-cyclohexenone system, see: A.G. Schultz, and H. Lee Tetrahedron Lett. 33 1992 4397
    • (1992) Tetrahedron Lett. , vol.33 , pp. 4397
    • Schultz, A.G.1    Lee, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.