106914-51-6Relevant academic research and scientific papers
Microwave-assisted solid-phase D?tz benzannulation reaction: A facile synthesis of 2,3-disubstituted-1,4-naphthoquinones
Shanmugasundaram, Muthian,Garcia-Martinez, Israel,Li, Qingyi,Estrada, Abril,Martinez, Nancy E.,Martinez, Luis E.
, p. 7545 - 7548 (2005)
A microwave-assisted solid-supported D?tz benzannulation of chromium carbene complexes with various alkynes has been developed. The oxidative cleavage of the resulting resin-bound 1,4-naphthols affords 2,3-disubstituted-1, 4-naphthoquinone derivatives in good to moderate yields with high purities.
Bisketene Equivalents as Diels-Alder Dienes
Dissanayake, Isuru,Hart, Jacob D.,Becroft, Emma C.,Sumby, Christopher J.,Newton, Christopher G.
supporting information, p. 13328 - 13333 (2020/09/03)
2,5-Bis(tert-butyldimethylsilyloxy)furans are established as vicinal bisketene equivalents for application as dienes in the Diels-Alder reaction. Cycloaddition with olefinic dienophiles, under exceptionally mild conditions, enables convergent access to highly substituted para-hydroquinones in unprotected form via a one-pot Diels-Alder/ring-opening/tautomerization sequence. The synthesis of para-benzoquinones from acetylenic dienophiles, including benzynes, is also demonstrated, and 2,5-bis(tert-butyldimethylsilyloxy)pyrroles are established as competent dienes for the synthesis of para-iminoquinones. Application in natural product synthesis enables gram-scale access to the neuroprotective agent (±)-indanostatin.
A transition-metal mediated regioselective synthesis of phenyl quinones via sequential benzannulation and cross coupling reactions
Kin Shing Chan,Chi Ching Mak
, p. 2003 - 2016 (2007/10/02)
A synthetic route for the regioselective synthesis of polysubstituted quinones by the benzannulation and subsequent cross coupling reactions has been developed. Alkenyl chromium carbene complexes undergo regioselective benzannulation with 2-(trimethylsilyl)-1-phenylethyne with oxidative workup to yield silyl quinones which upon iodination with ICI produce iodoquinones. Subsequent Stille's and Suzuki's cross coupling reactions of these iodoquinones yield polysubstituted quinones.
