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Volumn 22, Issue 9, 2008, Pages 523-528

Application of the anionic homologous Fries-rearrangement to the synthesis of 3-alkylbenzofuran-2(3H)-ones

Author keywords

Alkylation; Benzofuran 2(3H) ones; Fries rearrangement; Metalation; Organolithiums; Regioselectivity

Indexed keywords

COMPUTER NETWORKS; ORGANOMETALLICS;

EID: 51349146135     PISSN: 02682605     EISSN: 10990739     Source Type: Journal    
DOI: 10.1002/aoc.1437     Document Type: Article
Times cited : (4)

References (30)
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    • 3-Monoalkyl-substituted benzofuran-2(3H)-ones are usually synthesized by the metalation of ortho-alkoxy-substituted phenylacetic acids (mainly nitriles or esters), followed by acidic work-up of the resulting reaction products. See, for example: S. A. Shaw, P. Aleman, J. Christy, J. W. Kampf, P. Va, E. Vedejs.J.Am. Chem. Soc. 2006, 128, 925. DOI: 10.1021/ja056150x;
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    • The reactivity of the intermediate organometal towards aldehydes was briefly investigated. Quenching the reaction mixture with PhCHO (1.2 equiv., -80 C), followed by acidic cyclization of the crude reaction mixture, led to the recovery of 3benzylidenebenzofuran-2(3H)-one, as an 85:15 mixture of (E)/(Z) diastereoisomers, characterized by comparison with literature data. Owing to the possibility to synthesize similar compounds by employing benzofuran-2(3H)-one as a starting material, we do not investigate further on this reactivity. M. Msaddek, M. Rammah, K.Ciamala, J. Vebrel, B. Laude, Synthesis 1997, 1495. DOI: 10.1055/s1997-1369.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.