The novel structural modification of pyridoxal via its cyclization into 2-acyl- and 2-heteroarylfuro[2,3-c]pyridines

Морковник, А. С.; Зубенко, А. А.; Диваева, Л. Н.; Карцев, В. Г.; Бородкин, Г. С.; Клименко, А. И.

doi:10.1016/j.mencom.2019.01.040

Cited by 2 publications

(1 citation statement)

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“…Morkovnik and co-workers also reported the synthesis of the furo[2,3- c ]pyridine scaffold but via base-catalyzed cyclization of pyridoxal with acylmethyl halides and halomethylheteroarenes. The 2-acyl- and 2-heteroarylfuro[2,3- c ]pyridines 18 synthesized in this reaction were further elaborated to 4-aminomethyl-2-heteroaryl[2,3- c ]pyridines. 19 It is noteworthy to mention that the “unusual GBB-MCR” is the first and the only report that generates 2,3-diamine-substituted furo[2,3- c ]pyridines.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Triazolo[4′,5′:4,5]furo[2,3-c]pyridine via Post Modification of an Unusual Groebke–Blackburn–Bienaymé Multicomponent Reaction

Batra,

Kaur,

Kaushik

et al. 2024

ACS Omega

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The Groebke−Blackburn−Bienaymé(GBB) reaction is a well-established three-component reaction for synthesizing imidazofused scaffolds from heterocyclic amidines, aldehydes, and isonitriles. However, the replacement of pyridoxal as an aldehyde component in this reaction results in the formation of the furo[2,3-c]pyridine skeleton as an "unusual GBB product". Despite the interesting nature of this unusual reaction, not much work was further reported. The present research investigates the optimization strategy for the synthesis of novel tricyclic triazolo[4′,5′:4,5]furo[2,3-c]pyridines via diazotization of 2,3-diamino-furo[2,3c]pyridines specifically synthesized utilizing the chemistry of tert-alkyl isocyanide.

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Section: Introductionmentioning

confidence: 99%