202396-06-3Relevant articles and documents
Stereoselective synthesis of highly substituted cyclopentenones through [4+1] annulations of trialkylsilyl vinyl ketenes with α-benzotriazolyl organolithium compounds
Davie, Christopher P.,Danheiser, Rick L.
, p. 5867 - 5870 (2005)
Closing the ring: Highly functionalized cyclopentenones are prepared by the reaction of readily available metalated benzotriazole derivatives with trialkylsilyl vinyl ketenes (see scheme; Z = heteroatom substituent). Dienolate intermediates are generated
Convenient one-pot method for the preparation of polysubstituted benzo[b]- and naphtho[1,2-b]-furans and -thiophenes
Katritzky, Alan R.,Serdyuk, Larisa,Xie, Linghong
, p. 1059 - 1064 (2007/10/03)
N-(Phenoxymethyl)- and N-(phenylthiomethyl)-benzotriazoles are versatile substrates for the preparation of benzofurans and benzothiophenes by insertion reactions of their anions into alkyl and aryl aldehydes and in situ cyclization of the α-aryloxy and α-arylthio ketones thus formed. N-(Naphthyloxy)- and N-(naphthylthio)-benzotriazoles are similarly efficient precursors for naphthofurans and naphthothiophenes.
Synthesis of β-Alkoxy Ketones and α′-Functionalized β-Alkoxy Ketones Utilizing Benzotriazole-Stabilized Acyl Anion Synthons
Katritzky, Alan R.,Feng, Darning,Qi, Ming
, p. 1473 - 1477 (2007/10/03)
1-(α-Alkoxyalkyl)benzotriazoles 1a-d add to phenyl vinyl ether to form key intermediates 4a-d, which readily undergo lithiation and subsequent trapping by a variety of electrophiles to give the expected substituted derivatives 7a-d, 9a-c, 11, 13, 15, and 18 in high yields. Subsequent hydrolysis of these compounds provides a novel high-yield acyl anion synthon approach for the synthesis of β-alkoxy ketones 8 or α′-functionalized β-alkoxy ketones 10, 12, 14, 16, and 19 by short procedures from readily available starting materials.
