Synthesis and fungicidal activity of pseudo-thiohydantoins, their 5-arylidene derivatives, and 5-arylidene-3-β-aminothiazolid-2,4-one hydrochlorides

Abstract

A series of pseudo-thiohydantoins and their 5-arylidene derivatives have been synthesized. Reactions of acid hydrolysis of pseudo-thiohydantoins with the formation of the corresponding 5-arylidene-3-b-aminothiazolid-2,4-one hydrochlorides have been performed. The antifungal activity of the synthesized compounds has been evaluated.

Identification of (Z)-2-benzylidene-dihydroimidazothiazolone derivatives as tyrosinase inhibitors: Anti-melanogenic effects and in silico studies

“…First, 5,6-dihydroimidazo[2,1- b ]thiazol-3(2 H )-one ( 2 ) [67] , the DHIT template, was prepared by reacting 2-thioimidazolidine with ethyl chloroacetate in the presence of sodium acetate (yield 72%) ( Scheme 1 ) [68] . Reaction of 2 with benzaldehydes under Knoevenagel condensation conditions using sodium acetate/acetic acid gave benzylidene derivatives 1a – 1 k (all bearing the DHIT template) in yields of 37 to 88% [69] . To examine the effects of substituents of the benzylidene moiety on tyrosinase inhibition, various benzaldehydes bearing substituents such as a hydroxyl, a methoxyl, and/or an ethoxyl group were condensed with 2 .…”

Thiazolo[3,2-a]benzimidazoles: Synthetic Strategies, Chemical Transformations and Biological Activities

“…Acid hydrolysis of arylidene derivatives 55 lead to the formation of hydrochlorides of the corresponding thiazolid-2,4-ones 205 via the rupture of endocyclic C=N bonds in imidazole ring [ 96 , 97 ] ( Scheme 59 ).…”

Selective 5‐Exo‐Dig versus 6‐Endo‐Dig Cyclization of Benzoimidazole Thiols with Propargyl Alcohols

“…[23][24][25][26][27] In this paper, we reported an inexpensive and environmentally friendly synthetic method for the synthesis of benzothiazolo derivatives 3 or 4 using a Lewis acid-promoted reaction of benzoimidazole thiols with propargyl alcohol derivatives (Scheme 1). Benzothiazole derivatives show a large range of biological activities, such as antimicrobial, [28] antifungal, [29] antioxidant, [30] antiinflammatory [31] antidepressant, [32] anticonvulsant, [33] antitumor, [34] and anticancer. [35] To Scheme 1.…”

“…In this paper, we reported an inexpensive and environmentally friendly synthetic method for the synthesis of benzothiazolo derivatives 3 or 4 using a Lewis acid‐promoted reaction of benzoimidazole thiols with propargyl alcohol derivatives (Scheme 1). Benzothiazole derivatives show a large range of biological activities, such as antimicrobial, [28] antifungal, [29] antioxidant, [30] antiinflammatory [31] antidepressant, [32] anticonvulsant, [33] antitumor, [34] and anticancer [35] . To date, the most powerful and versatile processes for the synthesis of benzothiazolo imidazole are the cyclocondensation of N ‐(propynyl)‐o‐phenylenediamines with phenyl isothiocyanate, [36] NHC‐catalyzed [3+3] annulation of mercaptobenzimidazoles with alkynyl acylazoliums, [37] palladium‐catalyzed cyclocarbonylation of 2‐(propynylthio)‐1 H ‐benzo[ d ]imidazoles, [38,39] copper‐catalyzed cyclization of 2‐alkynyl‐3,3‐difluoro‐3 H ‐indole and mercaptoimidazole, [40] organocatalytic cyclizations of 2‐alkynyl‐3,3‐difluoro‐3 H ‐indoles with mercaptoimidazole, [41] palladium‐catalyzed multicomponent reactions of 2,4‐dichloroquinazoline, terminal alkynes, secondary amines, and mercaptoimidazole [42] .…”