Directed ortho metalation-cross coupling links. Carbamoyl rendition of the Baker-Venkataraman rearrangement. Regiospecific route to substituted 4- hydroxycoumarins

Tetrahedron Letters

Volumn 39, Issue 28, 1998, Pages 4995-4998

  Kalinin, Alexey V ^a   Da Silva, Alcides J M ^b   Lopes, Claudio C ^b   Lopes, Rosangela S C ^b   Snieckus, Victor ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

^b FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYCOUMARIN; CARBAMIC ACID DERIVATIVE; NATURAL PRODUCT;

ARTICLE; COUPLING FACTOR; CRYSTALLIZATION; DRUG ACTIVITY; DRUG SYNTHESIS; GENE REARRANGEMENT; NONHUMAN; STRUCTURE ANALYSIS;

EID: 0032500061     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00977-0     Document Type: Article

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32. 15. For example (see ref 14a), Fries rearrangement of 2-OMe and 3-Cl phenol esters affords 5-and 6-acylated products respectively (compare 6d and 6g).
33. 16. The DoM - Negishi route to ortho-acyl arylcarbamates also serves as an effective route to ortho-hydroxyarylacetophenones, e.g. 6e → 9, whose value for the synthesis of such complex polysubstituted derivatives as well as natural products is amply recognized, see Martin, R. Handbook of Hydroxyacetophenones, Kluwer Academic: Dordrecht. 1997 and Mincheva, Z.; Velkov, J.; Boireau, G.; Barry, J.; Fugier, C. Synth. Commun. 1995, 25, 149-156. (equation presented)
34. 16. The DoM - Negishi route to ortho-acyl arylcarbamates also serves as an effective route to ortho-hydroxyarylacetophenones, e.g. 6e → 9, whose value for the synthesis of such complex polysubstituted derivatives as well as natural products is amply recognized, see Martin, R. Handbook of Hydroxyacetophenones, Kluwer Academic: Dordrecht. 1997 and Mincheva, Z.; Velkov, J.; Boireau, G.; Barry, J.; Fugier, C. Synth. Commun. 1995, 25, 149-156. (equation presented)