478033-10-2Relevant academic research and scientific papers
Synthesis of carbo- and heterofused 5-amino-2H-1,2-thiazine 1,1-dioxides via the CSIC reaction strategy
Chuchvera, Yaroslav O.,Dobrydnev, Alexey V.,Dyachenko, Maksim S.,Frolov, Andriy I.,Ostapchuk, Eugeniy N.,Popova, Maria V.,Volovenko, Yulian M.
, (2022/02/21)
Herein, we present a full account of our studies with respect to the synthesis of carbo- and heterofused β-enamino-δ-sultams annelated on face c (3,4-bond). This class of compounds was designed as isomeric counterpart of known pharmacological templates – fused δ-sultams annelated through a face e (5,6-bond) following the principles of bioisosteric replacement. The starting material for this synthesis is cyclic vicinal amino nitriles. In particular, several methods were developed for methanesulfonylation of 5- and 6-membered carbo- and heteroaromatic as well as sp3-enriched β-enamino nitriles depending on their chemical nature and reactivity. The obtained N-mono- or/and N,N-dimesylates were converted into the corresponding N-methylmethanesulfonamides, which were subjected to the CSIC (Carbanion-mediated Sulfonate (Sulfonamide) Intramolecular Cyclization) reaction protocols thus affording target carbo- and heterofused β-enamino-δ-sultams. Their synthetic utility was demonstrated by the reactions with carbo- and hetero electrophiles.
