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Volumn 81, Issue 11, 2008, Pages 1512-1517

Synthesis of aromatic compounds using combinations of ring-closing olefin metathesis, dehydration, oxidation, and tautomerization

Author keywords

[No Author keywords available]

Indexed keywords

7-DIENE; ALLYLATION; CYCLIZED PRODUCTS; CYCLOHEXENE; HIGH YIELDS; OLEFIN METATHESIS; RCM REACTIONS; SUBSTITUTED BENZENES; TAUTOMERIZATION;

EID: 58149299312     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.81.1512     Document Type: Article
Times cited : (15)

References (66)
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    • For a comprehensive review, see; Modern Arene Chemistry, ed. by D. Astrac, Wiley-VCH, Weinheim, 2002.
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    • For a comprehensive review, see: a Handbook of Metathesis, ed. by R. H. Grubbs, Wiley-VCH, Weinheim, 2003. For reviews, see:
    • For a comprehensive review, see: a) Handbook of Metathesis, ed. by R. H. Grubbs, Wiley-VCH, Weinheim, 2003. For reviews, see:
  • 23
    • 23044511582 scopus 로고    scopus 로고
    • For reports on the pharmaceutical application of RCM in multi-kilogram scale (>400kg of cyclized product), see: a) T. Nicola, M. Brenner, K. Donsbach, P. Kreye, Org. Process Res. Dev. 2005, 9, 513.
    • For reports on the pharmaceutical application of RCM in multi-kilogram scale (>400kg of cyclized product), see: a) T. Nicola, M. Brenner, K. Donsbach, P. Kreye, Org. Process Res. Dev. 2005, 9, 513.
  • 28
    • 7044241256 scopus 로고    scopus 로고
    • For reports on the direct synthesis of carbocyclic aromatic compounds using RCM, see: a
    • For reports on the direct synthesis of carbocyclic aromatic compounds using RCM, see: a) A. Iuliano, P. Piccioli, D. Fabbri, Org. Lett. 2004, 6, 3711.
    • (2004) Org. Lett , vol.6 , pp. 3711
    • Iuliano, A.1    Piccioli, P.2    Fabbri, D.3
  • 33
    • 33745442211 scopus 로고    scopus 로고
    • For reports using RCM/elimination protocol, see
    • Angew. Chem., Int. Ed, 2006, 45, 2923. For reports using RCM/elimination protocol, see:
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 2923
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    • 34547168022 scopus 로고    scopus 로고
    • For a report using RCM/tautomerization protocol, see
    • l) S. Kotha, V. R. Shah, K. Mandal, Adv. Synth. Catal. 2007, 349, 1159. For a report using RCM/tautomerization protocol, see:
    • (2007) Adv. Synth. Catal , vol.349 , pp. 1159
    • Kotha, S.1    Shah, V.R.2    Mandal, K.3
  • 42
    • 33751205329 scopus 로고    scopus 로고
    • For selected recent reports on the synthesis of heterocyclic aromatic compounds using RCM, see: a
    • For selected recent reports on the synthesis of heterocyclic aromatic compounds using RCM, see: a) M. Arisawa, A. Nishida,M. Nakagawa, J. Organomet. Chem. 2006, 691, 5109.
    • (2006) J. Organomet. Chem , vol.691 , pp. 5109
    • Arisawa, M.1    Nishida, A.2    Nakagawa, M.3
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    • 58149310288 scopus 로고    scopus 로고
    • It must be noted that two-step yields of 4 from 2 via 6 were better than those via 3 with the exception of the special case of 4f, see: Ref. 9.
    • It must be noted that two-step yields of 4 from 2 via 6 were better than those via 3 with the exception of the special case of 4f, see: Ref. 9.
  • 56
    • 58149309751 scopus 로고    scopus 로고
    • The mesylated phenol was obtained under the conditions
    • The mesylated phenol was obtained under the conditions.
  • 57
    • 58149292768 scopus 로고    scopus 로고
    • The reason why we chose 2h and 2i as substrates to investigate these sequential experiments is that we observed that both intermediates 6h and 6i were somewhat unstable to isolation.
    • The reason why we chose 2h and 2i as substrates to investigate these sequential experiments is that we observed that both intermediates 6h and 6i were somewhat unstable to isolation.
  • 58
    • 58149283809 scopus 로고    scopus 로고
    • Attempts to obtain 8f from 6f at once were unsuccessful. For example, Swern oxidation of 6f gave a mixture of 4f, 5f (major), and 8f.
    • Attempts to obtain 8f from 6f at once were unsuccessful. For example, Swern oxidation of 6f gave a mixture of 4f, 5f (major), and 8f.
  • 59
    • 58149307253 scopus 로고    scopus 로고
    • The cyclized product 6b is also a potential precursor of resorcinol derivative. However, the synthesis of 8b from 6b was unfortunately unsuccessful. Although we have screened various oxidation conditions, the formation of phenol derivative 5b preferentially occurred.
    • The cyclized product 6b is also a potential precursor of resorcinol derivative. However, the synthesis of 8b from 6b was unfortunately unsuccessful. Although we have screened various oxidation conditions, the formation of phenol derivative 5b preferentially occurred.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.