638133-04-7Relevant articles and documents
Construction of Saturated Oxazolo[3,2-b][1,2]oxazines via Tandem [3+2]-Cycloaddition/[1,3]-Rearrangement of Cyclic Nitronates and Ketenes
Malykhin, Roman S.,Golovanov, Ivan S.,Nelyubina, Yulia V.,Ioffe, Sema L.,Sukhorukov, Alexey Yu.
, p. 16337 - 16348 (2021/12/02)
Reaction of six-membered cyclic nitronates with disubstituted ketenes affords hitherto unknown saturated oxazolo[3,2-b][1,2]oxazines possessing up to four contiguous stereogenic centers. The process involves a tandem of [3+2]-cycloaddition across the Ca? O bond of ketene, followed by a spontaneous [1,3]-rearrangement of transient vinylidene-substituted bicyclic nitrosoacetals. DFT calculations of the mechanism suggest that the [1,3]-O,C-shift proceeds through a recyclization of a biradical intermediate formed by an unusually mild homolytic cleavage of the N-O bond. The resulting products can be utilized as precursors of other fused 1,2-oxazines derivatives, in particular 1,2-oxazino-1,2,4-triazin-3-ones.
Synthesis of α-Thiooximes by Addition of Thiols to N, N -Bis(oxy)-enamines: A Comparative Study of S-, N-, and O-Nucleoa-philes in Michael Reaction with Nitrosoalkene Species
Naumovich, Yana A.,Kokuev, Aleksandr O.,Sukhorukov, Alexey Yu.,Ioffe, Sema L.
supporting information, p. 1334 - 1339 (2018/04/19)
Nucleophilic addition of thiols to N, N -bis(oxy)enamines (nitrosoalkene acetals) produce valuable α-thiooximes in a highly efficient manner. The reaction was found to be solvent-dependent, likely because of distinct mechanisms operating in nonpolar and basic solvents (involving either Bronsted acid or Lewis base catalysis). By performing a series of competition experiments, the relative reactivity of S-, N-, and O-nucleophiles in reaction with N, N -bis(oxy)enamines was determined for the first time. Interestingly, the relative nucleophilicity was found to be highly dependent on the solvent, which allows regioselective control of these reactions by using an appropriate medium.
Synthesis and characterization of novel 1,2-oxazine-based small molecules that targets acetylcholinesterase
Sukhorukov, Alexey Yu.,Nirvanappa, Anilkumar C.,Swamy, Jagadish,Ioffe, Sema L.,Nanjunda Swamy, Shivananju,Basappa,Rangappa, Kanchugarakoppal S.
, p. 3618 - 3621 (2014/07/22)
Thirteen 2-oxazine-based small molecules were synthesized targeting 5-lipoxygenase (LOX), and acetylcholinesterase (AChE). The test revealed that the newly synthesized compounds had potent inhibition towards both 5-LOX and AChE in lower micro molar concen
