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NMR characterization of new 10‐membered‐ring macrolactones and dihydrobenzophenazine‐5‐one, oxidized derivatives of benzo[ a ]phenazines
Author(s) -
Goulart Marília O. F.,
Machado Reys José Rui,
Emery Flavio S.,
Pinto Antônio V.,
de Souza Filho José Dias
Publication year - 2004
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1395
Subject(s) - chemistry , phenazine , heteronuclear single quantum coherence spectroscopy , ring (chemistry) , carbon 13 nmr , stereochemistry , proton nmr , oxide , two dimensional nuclear magnetic resonance spectroscopy , organic chemistry
Peroxidation of the phenazine of β‐lapachone using m ‐ClC 6 H 4 CO 3 HCH 2 Cl 2 furnished a macrolactone with a rigid 10‐membered ring, and the corresponding N ‐oxide, along with a dihydrobenzophenazine‐5‐one. All of the new compounds were fully characterized by spectroscopic methods, with the unambiguous assignment of the hydrogens and carbon NMR signals for the N ‐oxide, with the aid of 2‐D NMR, mainly COSY, HMQC, HSQC and HMBC. For the other two compounds some signals could not be assigned owing to their own intrinsic features. Copyright © 2004 John Wiley & Sons, Ltd.