Multicomponent Efficient Synthesis of New [1,2,4]Triazolo[3,4]thiadiazines

Abstract

A series of novel triazolo thiadiazines were synthesized by a simple, highly efficient, one‐pot pseudo four component approach involving the condensation of 4‐amino‐5‐hydrazinyl‐4H‐1,2,4‐triazole‐3‐thiol (1), aromatic aldehydes (2), and various phenacyl bromides (3) with good yields. The structures of compounds were confirmed by analytical and spectral (IR, 1H NMR, 13C NMR) data.

Synthetic Methods and Pharmacological Potentials of Triazolothiadiazines: A Review

“…Similarly, triazolothiadiazine hydrazone derivatives 77 were produced via a one-pot four component approach involving the condensation of 68 , aromatic aldehydes and various phenacyl bromides in absolute EtOH containing Et 3 N [ 62 ] ( Scheme 34 ).…”

“…The mechanism of producing compound 77 is described in the Scheme. Firstly, dianils 78 were formed; then a nucleophilic substitution reaction between the latter dianils and phanacyl bromide was followed by an annulation reaction via intermediates 79 and 80 [ 62 ] ( Scheme 35 ).…”

“…On the other hand, a series of triazolothiadiazine hydrazone derivatives 76 was synthesized via a one-pot, three-components reaction of Purpald 68, phenacyl bromides, and various aromatic aldehydes in EtOH at a reflex temperature [60,61] (Scheme 33). Similarly, triazolothiadiazine hydrazone derivatives 77 were produced via a one-pot four component approach involving the condensation of 68, aromatic aldehydes and various phenacyl bromides in absolute EtOH containing Et3N [62] (Scheme 34). On the other hand, a series of triazolothiadiazine hydrazone derivatives 76 was synthesized via a one-pot, three-components reaction of Purpald 68, phenacyl bromides, and various aromatic aldehydes in EtOH at a reflex temperature [60,61] On the other hand, a series of triazolothiadiazine hydrazone derivatives 76 was synthesized via a one-pot, three-components reaction of Purpald 68, phenacyl bromides, and various aromatic aldehydes in EtOH at a reflex temperature [60,61] (Scheme 33).…”

Vision on Synthetic and Medicinal Facets of 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazine Scaffold

“…A simple, multicomponent efficient synthesis of [1,2,4]triazolo[3,4- b ]thiadiazines ( 54 ) was reported by Sujatha et al [ 42 ] involving pseudo four component condensation of ( 44 ), aromatic aldehydes ( 2 ), and various phenacyl bromides ( 6 ) in presence of triethyl amine in absolute ethanol to afford novel [1,2,4]triazolo[3,4- b ]thiadiazine derivatives in excellent yields (Scheme 23 ). Shorter reaction time, good yields, operational simplicity, mild and clean reaction profiles are some key features of this method.…”

Discovery of ( ±)-3-(1H-pyrazol-1-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazine derivatives with promising in vitro anticoronavirus and antitumoral activity

“…We recently reported the synthesis of [1,2,4]triazolo [3,4b] [1,3,4]thiadiazines through the multi-component reaction (MCR) process [45]. The presence of a hydrazino group in these molecules offers the possibility to convert them into pyrazole moieties.…”