Synthesis and Conformational Behaviour of Enantiomeric Naphthoxazinoquinoxalinone Derivatives. Issue 37 (4th October 2017)

• Record Type: Journal Article
• Authors: Szatmári, István; Barta, Petra; Tóth, Gábor; Balázs, Attila; Halász, Judit; Fülöp, Ferenc
• Is Part Of: European journal of organic chemistry. Issue 37(2017)
• Page Start: 5537
• Page End: 5545
• Publication Date: 2017-10-04
• Subjects: Cycloaddition -- Quinones -- Microwave chemistry -- Fused‐ring systems -- Conformation analysis -- Heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700699
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : New non‐racemic naphth[1, 3]oxazino[3, 2‐ a ]quinoxalinones have been synthesized starting from an enantiomeric hexahydroquinoxalinone and 1‐aminoalkyl‐2‐naphthols or 2‐aminoalkyl‐1‐naphthols. The enantiopure annelational analogues naphth[1, 3]oxazino[3, 4‐ a ]quinoxalinone derivatives were also synthesized from the reactions of naphthols and the non‐racemic quinoxalinone followed by a ring‐closing reaction with formaldehyde. In addition to the study of the conformational behaviour of the new heteropolycycles, the diastereoselectivity and formation of the possible diastereomers were examined by NMR analysis. Theoretical calculations were performed to confirm the experimental results. Abstract : New non‐racemic naphth[1, 3]oxazino[3, 2‐ a ]quinoxalinones have been synthesized via an o ‐quinone methide intermediates. The enantiopure annelational analogues naphth[1, 3]oxazino[3, 4‐ a ]quinoxalinone derivatives have also been prepared by a different synthetic pathway. The conformational behaviour of the new polyheterocycles was examined and confirmed by theoretical calculations.