A General Way to Construct Arene‐Fused Seven‐Membered Nitrogen Heterocycles. Issue 3 (18th January 2018)

• Record Type: Journal Article
• Authors: Bakulina, Olga; Chizhova, Maria; Dar'in, Dmitry; Krasavin, Mikhail
• Is Part Of: European journal of organic chemistry. Issue 3(2018)
• Page Start: 362
• Page End: 371
• Publication Date: 2018-01-18
• Subjects: Nitrogen heterocycles -- Multicomponent reactions -- Fused‐ring systems -- Molecular diversity -- Imines -- Anhydrides; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701642
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Imines react with seven‐membered cyclic anhydrides (prepared from the corresponding dicarboxylic acids by a recently discovered in‐situ cyclodehydration protocol) by the Castagnoli–Cushman reaction pathway to give privileged seven‐membered arene‐fused nitrogen‐heterocyclic compounds with reagent‐controlled diversity of the skeleton and peripheral groups. Abstract : 3‐( o ‐Carboxyphenyl)propionic acid and four of its heteroatom‐containing analogs, as well as benzene‐ring‐fused analogs, have been shown to undergo a Castagnoli–Cushman reaction when dehydrated in the presence of an imine using acetic anhydride. This provides a facile, diastereoselective route to skeletally diverse arene‐fused ε‐lactams.