Green, one-pot synthesis of 1,2-oxazine-type herbicides via non-catalyzed Hetero Diels-Alder reactions comprising (2E)-3-aryl-2-nitroprop-2-enenitriles
Przemysław Woliński, Agnieszka Kącka‐Zych, Barbara Mirosław, Ewelina Wielgus, Aleksandra Olszewska, Radomir Jasiński
Abstract
In the framework of this paper we describe a new, green procedure for the synthesis of a series of 1,2-oxazine N-oxide moieties via Hetero Diels-Alder (HDA) reaction with the participation of (2E)-3-aryl-2-nitroprop-2-enenitriles. For the contrast of most known HDA reactions, the described process is realized without presence of Lewis acid-type catalyst as well as under mild conditions, with full atomic economy and selectivity. Additionally, we established, that the reaction process can be characterized with Molecular Electron Density Theory (MEDT).
Topics & Concepts
CatalysisArylChemistrySelectivityDiels–Alder reactionOxideOrganic chemistryCombinatorial chemistryAlkylSynthesis and Biological EvaluationOrganic Chemistry Cycloaddition ReactionsChemical Reaction Mechanisms