Synthesis and Regioselectivity in the Alkylation of 1,3,4‐Oxadiazolethiones with Dihaloalkanes and Epichlorohydrin

Abstract

The regioselectivity in the alkylation of 1,3,4‐oxadiazolethiones with dihaloalkanes was found that it depends mainly on the length of the alkyl chain connecting the two halides; moreover, the formation of thiirane ring instead of epoxide ring during the alkylation with epichlorohydrin was surprising.

Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition

“…As part of our current studies on the development of new routes in heterocyclic synthesis, − here we focused on the synthesis of new heterocyclic systems from ninhydrin. Stirring ninhydrin 1 with ethyl acetoacetate 2 in water for 15 min afforded ethyl indeno­[1,2- b ]­furan-3-carboxylate 3 in excellent yield .…”

Finding the right balance between tertiary amine steric effect and solvent polarity for the regioselectivity and kinetics of epichlorohydrin acetolysis

“…1,2 The high reactivity of the three-membered ring provides the use of ECH to obtain di-and trifunctional organic compounds, polyfunctional polymers, and composites based on them 2,3 to develop effective methods for the synthesis of new heterocyclic and macrocyclic molecules. [4][5][6][7][8][9] The reactions of epichlorohydrin with proton-containing reagents (carboxylic acids, alcohols, phenols) are widely used for the synthesis of biologically active substances that exhibit antibacterial, antituberculous, and antimalarial properties, act as antioxidants and enzyme inhibitors, and are included to hypoglycemic drugs. 1,[10][11][12] The oxirane ring opening by carboxylic acids occurs to form two regioisomeric chlorohydrin esters (Scheme 1).…”