Synthetic Studies Towards the Preparation of 2‐Benzyl‐2‐hydroxybenzofuran‐3(2H)‐one, the Prototype of Naturally Occurring Hydrated Auronols.

Loeser, Reik; Chlupáčová, Marta; Mareček, Aleš; Opletalová, Veronika; Guetschow, Michael

doi:10.1002/chin.200507094

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2019

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“…Azadienes 1 could be synthesized from enones and sulfonamides according to the known literature procedures. 9,11,12 Among them, azadienes 1a−d, 9a 1e, 9i 1f− j, 9a 1k, 9r 1l, 9j 1m, 9c and 1n 9i are the known compound. Starting materials benzofuran-3(2H)-ones 12 and intermediate enones 9j,11 are the known compounds.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Copper-Catalyzed Alkynylation/Cyclization/Isomerization Cascade for Synthesis of 1,2-Dihydrobenzofuro[3,2-b]pyridines and Benzofuro[3,2-b]pyridines

Xie

Sun

et al. 2019

J. Org. Chem.

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An efficient copper-catalyzed cascade alkynylation/cyclization/isomerization reaction of aurone-derived azadienes with terminal alkynes has been developed, giving a series of 1,2-dihydrobenzofuro[3,2-b]pyridines with excellent yields. The obtained 1,2-dihydrobenzofuro[3,2-b]pyridines can be conveniently transformed into the corresponding benzofuro[3,2-b]pyridines under basic conditions. Additionally, benzofuro[3,2-b]pyridines can also be prepared from azadienes and terminal alkynes in a one-pot reaction. The synthetic utility was demonstrated by the synthesis of three bioactive molecules with potent topoisomerase inhibition in high yields. This strategy provides a facile approach to 1,2-dihydrobenzofuro[3,2-b]pyridines and benzofuro[3,2-b]pyridines.

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Section: ■ Experimental Sectionmentioning

confidence: 99%