Microwave-Assisted Solid-Phase Dötz Benzannulation Reaction

• DOI: 10.1055/s-2005-921703
• Publication Date: 2009-04-16T09:45:06Z
• Authors: L. Martinez; M. Shanmugasundaram; I. Garcia-Martinez; Q. Li; A. Estrada; N. Martinez
• Keywords: Ammonium nitrate; Solid-Phase Synthesis

A microwave-assisted solid-phase Dötz benzannulation reaction using a resin-bound chromium carbene complex was demonstrated. The cyclization of Wang resin-supported Fischer 1 with various alkynes 2 followed by subsequent treatment cerium(IV) ammonium nitrate (CAN) gave naphthoquinone derivatives 4 in moderate yields without the formation indenes, indenones or cyclobutenones as side products. 1,4-diphenyl butadiyne (R1 = Ph, R2 C≡CPh) cleanly afforded mono product 68% yield any intermolecular double benzannulations cyclo­butenone formation.