Annulation Cascade of Sulfamate-Derived Cyclic Imines with Glycine Aldimino Esters: Synthesis of 1,3-Benzoxazepine Scaffolds
Mallu Kesava Reddy, Vinod Bhajammanavar, Mahiuddin Baidya
Abstract
An efficient (3 + 2) cycloaddition triggered annulation is reported to access 1,3-benzoxazepine frameworks. With amine base, sulfamate-derived cyclic imines readily react with glycine aldimino esters to furnish benzo-fused seven-membered heterocyclic products in good yields. The cascade reaction involves the formation of one C–C, one C–N, and one C–O bond along with the cleavage of two C–N bonds and one S–O bond. The synthesis of o-tyrosine analogues has also been accomplished from annulation products.
Topics & Concepts
AnnulationChemistryCycloadditionCascadeGlycineCleavage (geology)Amine gas treatingBond cleavageStereochemistryCombinatorial chemistryBase (topology)Organic chemistryAmino acidCatalysisChromatographyEngineeringFracture (geology)BiochemistryGeotechnical engineeringMathematicsMathematical analysisSynthesis and Catalytic ReactionsSynthesis and Biological ActivitySynthesis of β-Lactam Compounds