Journal
ORGANIC LETTERS
Volume 20, Issue 13, Pages 3871-3874Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01452
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Funding
- National Institute of Health (NIH) [2R01GM097082-05]
- European Lead Factory (IMI) [115489]
- Qatar National Research Foundation [NPRP6-065-3-012]
- ITN Accelerated Early stage drug discovery (AEGIS) [675555]
- KVVF Kankerbestrijding grant [10504]
- European Regional Development Fund [POIG.02.01.00-12-023/08]
- [665250]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM097082] Funding Source: NIH RePORTER
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A series of unprecedented tetrazole-linked imidazo[1,5-a]pyridines are synthesized from simple and readily available building blocks. The reaction sequence involves an azido-Ugi-deprotection reaction followed by an acetic anhydride-mediated N-acylation-cyclization process to afford the target heterocycle. Furthermore, the scope of the methodology was extended to diverse R-3-substitutions by employing commercial anhydrides, acid chlorides, and acids as an acyl component. The scope for the postmodification reactions are explored and the usefulness of the synthesis is exemplified by an improved three-step synthesis of a guanylate cyclase stimulator.
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