Synthesis of Triazolo4',5':4,5furo2,3-cpyridine via Post Modification of an Unusual Groebke-Blackburn-Bienaymé Multicomponent Reaction

• Published in: ACS omega Vol. 9; no. 27; p. 29372
• Main Authors: Batra, Aashima, Kaur, Manpreet, Kaushik, Deepender, Kaur, Simran, Patil, Madhuri T, Chaudhari, Vinod D, Sahoo, Subash Chandra, Salunke, Deepak B
• Format: Journal Article
• Language: English
• Published: 09.07.2024
• ISSN: 2470-1343; 2470-1343
• DOI: 10.1021/acsomega.4c01359

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[2,3-c]pyridines specifically synthesized utilizing the chemistry of tert-alkyl isocyanide.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[2,3-c]pyridines specifically synthesized utilizing the chemistry of tert-alkyl isocyanide.