2,3-Dihydro-1,2,6-thiadiazine 1-Oxides by Biginelli-Type Reactions with Sulfonimidamides under Mechanochemical Conditions.
Biginelli-type multicomponent reactions (MCRs) with NH-free sulfonimidamides provide 2,3-dihydro-1,2,6-thiadiazine 1-oxides in high yields. The couplings are performed in a planetary ball mill under solvent-free mechanochemical conditions. Acetic acid or ytterbium triflate are used as catalysts. A representative product was characterized by X-ray single crystal structure analysis revealing molecular details of the highly functionalized three-dimensional heterocycle. Further product modifications lead to additional structural scaffolds.
[3+2]‐Cycloadditions of N ‐Cyano Sulfoximines with 1,3‐Dipoles
Involving the cyano group of N‐cyano sulfoximines in [3+2]‐cycloaddition reactions with 1,3‐dipoles provides practical routes for the construction of 5‐membered heterocycles bearing sulfoximinoyl moieties. An ytterbium‐catalyzed cycloaddition utilizing hydrazonoyl chlorides was developed, as well as a reaction involving imidoyl chlorides proceeding without the aid of a catalyst. Following these protocols, a range of sulfoximines with N‐1,2,4‐triazolyl and N‐1,2,4‐oxadiazolyl substituents was prepared. peerReviewed
CCDC 2062891: Experimental Crystal Structure Determination
Related Article: Felix Krauskopf, Khai-Nghi Truong, Kari Rissanen, Carsten Bolm|2021|Org.Lett.|23|2699|doi:10.1021/acs.orglett.1c00596
CCDC 1984075: Experimental Crystal Structure Determination
Related Article: Felix Krauskopf, Khai-Nghi Truong, Kari Rissanen, Carsten Bolm|2020|Eur.J.Org.Chem.|2020|2761|doi:10.1002/ejoc.202000335