Premium
Grafting Bis(heteroaryl) Motifs into Ring Structures
Author(s) -
Apte Chirag N.,
Diaz Diego B.,
Adrianov Timur,
Yudin Andrei K.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000838
Subject(s) - chemistry , phosphorane , ring (chemistry) , heteroatom , combinatorial chemistry , azole , molecule , stereochemistry , pyrazole , organic chemistry , antifungal , medicine , dermatology
Here we demonstrate an approach to graft bis(heteroaryl)‐containing motifs into ring structures. The process occurs by redirecting a previously reported oxadiazole‐forming reaction towards a pyrazole‐forming process affording pyrazolyl‐azole containing molecules. Through the use of ( N ‐isocyanimino)phosphorane (Pinc), heteroatom‐rich fused tricyclic heterocycles can be synthesized in a single step from readily accessible starting materials. The cyclization of peptides results in macrocycles that feature bis(heteroaryl) motifs with uncommon connectivity as compared to their natural counterparts.