메뉴 건너뛰기




Volumn , Issue 3, 2005, Pages 501-505

Tandem catalysis: A ring-closing metathesis followed by dehydrogenative oxidation to afford substituted indenones

Author keywords

Dehydrogenations; Indenols; Indenones; Metathesis; Ruthenium; Tandem reactions

Indexed keywords

1 (2 PROPENYLPHENYL)PROP 2 EN 1 OL DERIVATIVE; INDENE DERIVATIVE; INDENONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 14644404260     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-862356     Document Type: Article
Times cited : (38)

References (55)
  • 19
    • 14644404540 scopus 로고
    • Road's Chemistry of Carbon Compounds, 2nd Ed., 2nd Suppl., (partial)/IIIG/IIIH; Sainsbury, M., Ed.; Elsevier: Amsterdam
    • (a) Coombs, M. M. Benzocyclopropene, Benzocyclobutene and Indene, and their Derivatives, In Road's Chemistry of Carbon Compounds, 2nd ed., 2nd Suppl., Vol. IIIF(partial)/IIIG/IIIH; Sainsbury, M., Ed.; Elsevier: Amsterdam, 1995.
    • (1995) Benzocyclopropene, Benzocyclobutene and Indene, and Their Derivatives , vol.3 F
    • Coombs, M.M.1
  • 32
    • 14644403881 scopus 로고    scopus 로고
    • note
    • Work taken from the post-doctoral research project of Dr. E. M. Coyanis and the ongoing MSc project of Ms J.-L. Panayides.
  • 37
    • 14644426177 scopus 로고    scopus 로고
    • note
    • +], 179 (18), 178 (100), 177 (28), 176 (16), 163 (41), 161 (12), 149 (16), 147 (18), 146 (18), 135 (10), 118 (10), 77 (10), 69 (11), 57 (14), 55 (12), 43 (28), 41 (19).
  • 38
    • 14644417389 scopus 로고    scopus 로고
    • note
    • All new compounds were identified using routine spectroscopy and gave satisfactory data.
  • 39
    • 14644408300 scopus 로고    scopus 로고
    • note
    • In an attempt to improve the yields of indenols 6d and 6e we protected the alcohol functionalities of 5d and 5e with acetyl groups. However, much to our surprise, the RCM reactions of these substrates, at r.t. or at 110 °C, did not proceed to afford the acetyl-protected cyclic products and only starting material was recovered.
  • 40
    • 14644389855 scopus 로고    scopus 로고
    • note
    • +], 193 (21), 178 (20), 177 (40), 176 (100), 175 (25), 163 (17), 161 (23), 149 (37), 147 (20), 105 (21), 91 (17), 77 (26), 73 (23), 69 (22), 57 (33), 55 (26), 43 (49), 41 (46).
  • 41
    • 14644405181 scopus 로고    scopus 로고
    • note
    • -3. R1 = 0.0421, wR2 = 0.0813. Crystallographic data for the structure have been deposited with the Cambridge Crystallographic Data Centre as deposition No. CCDC-250072.
  • 42
    • 14644432663 scopus 로고    scopus 로고
    • note
    • Storage of the indenols (as oils) without the exclusion of air resulted in a slow conversion into indenones (ca. 5% over six months).
  • 43
    • 0000310627 scopus 로고
    • 23c have been successfully used to accomplish the indenol to indenone transformation. See (a) Wu, Y.; Ahlberg, P. Acta Chem. Scand. 1995, 49, 364.
    • (1995) Acta Chem. Scand. , vol.49 , pp. 364
    • Wu, Y.1    Ahlberg, P.2
  • 50
    • 0037272918 scopus 로고    scopus 로고
    • 8-toluene) was conducted on 5a (with catalyst 1) at 105 °C, evidence suggested that a ruthenium-promoted redox isomerization was occurring to form the corresponding indanone 8. See the following references describing this type of transformation mediated by ruthenium metathesis catalysts: (a) Greenwood, E. S.; Parsons, P. J.; Young, M. J. Synth. Commun. 2003, 33, 223.
    • (2003) Synth. Commun. , vol.33 , pp. 223
    • Greenwood, E.S.1    Parsons, P.J.2    Young, M.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.