1,3,5-Oxadiazines and 1,3,5-Thiadiazines

Controlled Synthesis of 1,3,5-Oxadiazin-2-ones and Oxazolones through Regioselective Iodocyclization of Ynamides

“…In addition, the stereochemistry was confirmed via single-crystal X-ray diffraction (for details, see the Supporting Information). Importantly, 1,3,5-oxadiazin-2-ones are classic and important six-membered heterocyclic compounds which are widely present in several areas, such as nature compounds and weight promoters . However, due to the lack of methods for the synthesis of 1,3,5-oxadiazin-2-ones, further application of the derivatives mentioned above has been restricted.…”

The Mannich-Type Synthesis of Macroheterocycles with Pyrido[2,1-b][1,3,5]thiadiazine Unit

“…Москва, Российская Федерация 1,3,5-Thiadiazines have attracted great attention due to a wide spectrum of biological activity (for reviews on the 1,3,5-thiadiazine chemistry, see [1][2][3][4] ). Recently we have found that thiolate 1 readily reacts with excess of formaldehyde HCHO and primary amines in boiling DMF to give 7,7'-bis(pyrido [2,1-b] [1,3,5]thiadiazinyl)methanes 2 [5] (Scheme 1).…”

Design and Synthesis of Pyrido[2,1-b][1,3,5]thiadiazine Library via Uncatalyzed Mannich-Type Reaction

“…1,3,5-Thiadiazines have attracted considerable attention over the years because of their biological activities and applications in medicine and agriculture (for reviews on the 1,3,5-thiadiazine chemistry, see refs − ). 1,3,5-Thiadiazines are known as antidermatophites, , antifungal and fungistatic agents, − antimicrobials and bactericides, − antifibrinolytic agents, − tuberculostatics, − etc.…”

“…One of the most effective approaches to 1,3,5-thiadiazines is based on the double Mannich-type reaction of thioamides, dithiocarbamates or related S , N -binucleophilic species with primary amines and formaldehyde. − Cyclic thioamides (γ- and δ-thiolactams, 2-mercaptoazoles, -azines, or their 2-thioxotautomers) can also be successfully employed in this reaction, giving rise to a variety of ring-condensed 1,3,5-thiadiazines. In fact, the related syntheses of 1,2,4-triazolo[3,4- b ][1,3,5]thiadiazines, − imidazo[2,1- b ][1,3,5]thiadiazines, , 1,2,4-triazino[3,2- b ][1,3,5]thiadiazines, thiazolo[3′,4′:1,5][1,2,4]triazolo[3,4- b ][1,3,5]thiadiazines, 1,3,5-thiadiazino[3,2- a ]benzimidazoles, cyclopenta[ g ]pyrido[2,1- b ][1,3,5]thiadiazines, bis (pyrido[2,1- b ][1,3,5]thiadiazin-7-yl)methanes, pyrimido[2,1- b ][1,3,5]thiadiazines, and pyrimido[4,3- b ][1,3,5]thiadiazines − have been reported (Scheme ).…”