147424-20-2Relevant academic research and scientific papers
Tautomerism and stereodynamics of indophenols, amidines, their derivatives, and analogs: XIII. 1 intramolecular cyclization of 2,6-di-tert-butyl-4-(o-alkoxyphenylimino)-2,5-cyclohexadienones as a method of synthesis of spiro benzoxazines
Kurbatov,Simakov,Vikrishchuk,Ruzhnikov,Zhdanov,Olekhnovich
, p. 776 - 779 (2007/10/03)
A new method was developed for synthesizing benzoxazine derivatives by O-alkylation of 2,6-di-tert-butyl-4-(o-hydroxyphenylirnino)-2,5-cyclohexadienones with allyl or benzyl halides and subsequent thermal heterocyclization of allyl or benzyl ethers thus f
TAUTOMERISM AND STEREODYNAMICS OF INDOPHENOLS, AMIDINES AND THEIR DERIVATIVES AND ANALOGS. X. NOVEL INTRAMOLECULAR REARRANGEMENT OF O-ALLYL AND O-BENZYL DERIVATIVES OF o-INDOPHENOLS
Olekhnovich, L. P.,Simakov, V. I.,Furmanova, N. G.,Ivakhnenko, E. P.,Rekhlova, O. Yu.,et al.
, p. 727 - 739 (2007/10/02)
We have observed for the first time that O-allyl and O-benzyl derivatives of o-indophenols, heated in solution to 100-150 deg C, when rapid degenerate ZE isomerization at the C=N bond occurs, suffer irreversible intramolecular rearrangement to form benzoxazine heterospiran systems.This transformation involves concerted elementary acts of -sigmatropic C -> N proton shift and electrocyclic formation of a C-C bond induced by the electronic polarization of the initial molecules in the process of ZE stereodynamics due to torsional rotation.The absolute configuration of new heterospirans is diastereospecific as a result of the exclusively pseudoequatorial orientation of the vinyl and aryl groups with respect to the cyclohexadienone fragment.
