682774-05-6Relevant articles and documents
Alkynyl triazenes enable divergent syntheses of 2-pyrones
Tan, Jin-Fay,Bormann, Carl Thomas,Severin, Kay,Cramer, Nicolai
, p. 9140 - 9145 (2021/07/12)
The 2-pyrone motif occurs frequently in bioactive natural products and is appreciated as synthetic intermediates. However, only few methods allow for diversifying functional group modifications on this relevant heterocycle. The distinct properties of 1-alkynyl triazenes promote a smooth addition of propiolic acids across the triple bond. Addition of catalytic amounts of silver salt induces cyclization to 2-pyrones. Depending on the reaction temperature, either 6-triazenyl or 5-triazenyl 2-pyrones are selectively formed. The triazenyl unit is subsequently replaced by a variety of valuable groups in a one-pot process yielding for instance 2-fluoro pyrones. The substitution occurs with an intriguing 1,5-carbonyl transposition. Moreover, the triazenyl group serves as traceless activating group for subsequent Diels-Alder cycloadditions and as a constituting unit for rare fused aminopyrazole pyrone heterocycles.
An efficient synthesis of substituted anthraquinones and naphthoquinones
Bailey, David,Williams, Vance E.
, p. 2511 - 2513 (2007/10/03)
An efficient synthesis of 6,7-disubstituted naphthoquinones and 2,3,6,7-tetrasubstituted anthraquinones were developed using the reaction of thiophene dioxides and benzoquinone and naphthoquinone derivatives, respectively.
