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Synthesis and structure of some imines containing furoxan ring derived from isosafrole
Author(s) -
Dinh Nguyen Huu,
Ly Ngo Thi,
Van Le Thi Thanh
Publication year - 2004
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570410628
Subject(s) - furoxan , chemistry , benzene , imine , ring (chemistry) , nitro , two dimensional nuclear magnetic resonance spectroscopy , stereochemistry , proton nmr , medicinal chemistry , organic chemistry , alkyl , nitric oxide , catalysis
A series of 14 imines containing furoxan and benzene rings has been prepared starting from isosafrole. The structure of reported compounds have been confirmed by elemental analysis, EI MS, UV, IR, and NMR spectroscopy. It is shown that, on treatment with Na 2 S 2 O 4 , the nitro group on the benzene ring was reduced to amino group, but the N→O group of the furoxan ring was not. The 1 H‐ and 13 C NMR signals are assigned based on their spin‐spin splitting patterns, in some cases, NOESY and HMBC spectra are used. The NOESY spectra indicate that for reported imines, the benzene and the furoxan rings could not be co‐planar; the imine group has E ‐configuration.