title: Synthesis of spirocyclic thiazolidinediones using ring-closing metathesis and one-pot sequential ring-closing/cross metathesis.
abstract: A novel synthetic route to spirocyclic thiazolidinediones is reported by utilizing ring-closing metathesis (RCM). A selective cross metathesis (CM) of N-allyl azaspiro derivatives with different olefins has been demonstrated to prepare substituted azaspiro-[4.4]nonenediones. The X-ray crystal structure of a spirocyclic thiazolidinedione dimer is described, which has been prepared in two steps from thiazolidinedione using a one-pot sequential ring-closing and self metathesis. Cross metathesis proceeds smoothly with both electron rich and poor olefins. The symmetrical bis-thiazolidinedione spirocyclic system can be used as CM coupling partner with olefins. One-pot sequential RCM-CM has been developed for the synthesis of substituted spirocyclic compounds. The methodology allows a quick access to thia-azaspiro-[4.4]nonene and -[4.5]decene-dione ring systems from readily available starting materials which are not otherwise accessible.
authors: Indian Institute of Science Education and Research Kolkata, Mohanpur Campus, Mohanpur, Nadia, West Bengal, India.
authors: Kalyan
authors: K
authors: Dhara
authors: Sushovan
authors: S
authors: Paladhi
authors: Ganesh Chandra
authors: GC
authors: Midya
authors: Jyotirmayee
authors: J
authors: Dash
mesh_terms: D001372:Aza Compounds / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D013141:Spiro Compounds / Q000737:chemistry*; D013379:Substrate Specificity; D045162:Thiazolidinediones / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D001372:Aza Compounds; D013141:Spiro Compounds; D045162:Thiazolidinediones; C089946:2,4-thiazolidinedione