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Synthesis and Conformational Behaviour of Enantiomeric Naphthoxazinoquinoxalinone Derivatives
Author(s) -
Szatmári István,
Barta Petra,
Tóth Gábor,
Balázs Attila,
Halász Judit,
Fülöp Ferenc
Publication year - 2017
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.201700699
Subject(s) - chemistry , enantiomer , stereochemistry
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.