Synthesis of chlorinated bicyclic C-fused tetrahydrofuro[3,2-c]azetidin-2-ones.
Some bicyclic C-fused chlorinated tetrahydrofuro[3,2-c]azetidin-2-ones were prepared by a fairly general route involving Staudinger reaction of allylic/propargylic imidates with dichloroketene followed by highly diastereoselective CuCl/PMDETA-catalyzed 5-exo-trig/dig chlorine atom transfer radical cyclization. An oxepan-fused β-lactam was also prepared similarly by 7-endo-trig cyclization. Synthetic application of the side chain chlorine atom of the products was demonstrated by its substitution in one of the products with azide followed by azide-alkyne click reaction with phenylacetylene to obtain a 1,2,3-triazolyltetrahydrofuro[3,2-c]azetidin-2-one.
Ram
Ram N
RN
Department of Chemistry, Indian Institute of Technology, Delhi, Hauz Khas, New Delhi 110016, India. rnram@chemistry.iitd.ernet.in
Kumar
Neeraj
N
Singh
Nem
N
D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D054879:Halogenation
C116379:2-azetidinone; D001384:Azetidines; D002244:Carbon; D003300:Copper