6533b7d0fe1ef96bd125b631

RESEARCH PRODUCT

5-Carbonyl-1,3-oxazine-2,4-diones from N-Cyanosulfoximines and Meldrum’s Acid Derivatives

Carsten BolmMariela BreguFelix BrosgeKhai-nghi TruongJohannes Florian KochsKari Rissanen

subject

Structure analysis010405 organic chemistryOrganic Chemistry010402 general chemistryMeldrum's acid01 natural sciencesBiochemistry0104 chemical scienceschemistry.chemical_compoundchemistryProduct (mathematics)Organic chemistryProduct formationPhysical and Theoretical Chemistry

description

At elevated temperatures, N-cyanosulfoximines react with Meldrum's acid derivatives to give sulfoximines with N-bound 5-carbonyl-1,3-oxazine-2,4-dione groups. A representative product was characterized by single-crystal X-ray structure analysis. The product formation involves an unexpected molecular reorientation requiring several sequential bond-forming and -cleaving processes.

https://doi.org/10.1021/acs.orglett.0c02504