Direct Exchange of Oxygen and Selenium Atoms in the 1,2,5-Oxadiazoles and 1,2,5-Selenadiazoles by Action of Sulfur Monochloride

Abstract

A short synthetic approach to fused 1,2,5-thiadiazoles from the corresponding 1,2,5-oxadiazoles and 1,2,5-selenadiazoles has been developed. Mono-and bis(1,2,5-thiadiazoles) were selectively obtained in high yields. The pathways for these novel reactions were discussed.

Synthesis and Applications of 5‐Membered Chalcogen‐Nitrogen π‐Heterocycles with Three Heteroatoms

“…In an attempted synthesis of 1,2,5‐oxadiazolo‐fused 1,2,5‐thiadiazole, the chalcogen exchange was observed leading to bis(1,2,5‐thiadiazole) (Scheme ) . This exchange made possible concise synthesis of bis(thiadiazolo)pyrazine (Scheme ) obtained earlier in 7 steps …”

Design and theoretical study of D–A–pi–A' organic sensitizers with [1,2,5]oxa-, thia- or selenadiazoloazine fragment

“…In our study we use both traditional building blocks reviewed previously by us and by other authors and extended list of donor groups that includes some new previously unexplored fragments. Based on our recent investigations and the works of other researchers 7,[14][15][16][17][18][19][20][21][22][23][24] six variants of A-fragments (A-block) which have showed good characteristics were selected for the present study: [1,2,5]thiadiazolo [3,4-c] [3,4-c]pyridazine. The general formula for these derivatives is represented in Scheme 1.…”

A tribute to Professor Oleg Alekseevich Rakitin

“…By using the DABCO/S 2 Cl 2 sufurization protocol Oleg was able to carry out one pot transformations of aromatic heterocycles (e.g., pyrroles and indoles) and also fully saturated heterocycles (e.g., pyrrolidines and tetrahydrothiophenes) into pentathiepins often in useful yields (Scheme 6). More recently, Oleg has investigated the formal exchange of chalcogens in fused 1,2,5-heterodiazoles, exemplified by the conversion of fused 1,2,5-oxadiazoles and 1,2,5-seleno-diazoles into 1,2,5-thiadiazoles, 31,32 and the interconversion of 1,2,5-thiadiazoles and 1,2,5-seleno-diazoles. 4,32,33 In collaboration with colleagues…”

“…More recently, Oleg has investigated the formal exchange of chalcogens in fused 1,2,5-heterodiazoles, exemplified by the conversion of fused 1,2,5-oxadiazoles and 1,2,5-seleno-diazoles into 1,2,5-thiadiazoles, 31,32 and the interconversion of 1,2,5-thiadiazoles and 1,2,5-seleno-diazoles. 4,32,33 In collaboration with colleagues…”