A STUDY ON THE 1,3-DIPOLAR CYCLOADDITIONS IN HETEROCYCLIC SYSTEMS
Abstract
THE MAIN PURPOSE OF THIS WORK IS TO STUDY THE 1,3-DIPOLAR CYCLOADDITION REACTIONS TO SUBSTITUTED EXOMETHYLENE-OXAZOLONES AND THIAZOLONES AND TO EXAMINE THESE REACTIONS AS A POSSIBLE SOURCE OF HETEROCYCLIC A-AMINOACID DERIVATIVES. (Z)- AND (E)-2- PHENYL-4-ARYLIDENE-5(4H)-OXAZOLONES REACT WITH NITRILIMINES AND (Z)-2-PHENYL-4-ARYLIDENE-5(4H)-THIAZOLONES WITH STABLE NITRILE OXIDES AND NITRILIMINES TO AFFORD SPIRO CYCLOADDUCTS, BY ADDITION OF THE DIPOLE ON THE EXOCYCLIC DOUBLE BOND. THE REACTIONS ARE STEREOSPECIFIC AND REGIOSELECTIVE, GIVING IN ALL CASES ONLY ONE REGIOISOMER, IN WHICH THE ANIONIC CENTER OF THE DIPOLE IS JOINED WITH THE TERTIARY CARBON ATOM OF OXAZOLONE-OR THIAZOLONE-RING. THE STRUCTURE OF THESE NEW COMPOUNDS WAS CONFIRMED BY SPECTROSCOPIC DATA AND BY CHEMICAL METHODS.THE OBSERVED REGIOCHEMISTRY IS ALSO RATIONALIZED BY FRONTIER MOLECULAR ORBITALCONSIDERATIONS OF THE REACTING SYSTEMS, USING EHMO-CALCULATIONS FOR THE MAGNITUDES OF OXAZOLONE ATOMIC ORBITAL COEFFICIENTS. ATTEMPT ...
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