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Review
. 2024 Mar 16;29(6):1326.
doi: 10.3390/molecules29061326.

Synthetic Methods and Pharmacological Potentials of Triazolothiadiazines: A Review

Mohamed S Mostafa  1 , Ibrahim Ali M Radini  1 , Naglaa M Abd El-Rahman  2 , Rizk E Khidre  2
Affiliations
Review

Synthetic Methods and Pharmacological Potentials of Triazolothiadiazines: A Review

Mohamed S Mostafa et al. Molecules. .

Abstract

This review article examines the synthetic pathways for triazolothiadiazine derivatives, such as triazolo[3,4-b]thiadiazines, triazolo[5,1-b]thiadiazines, and triazolo[4,3-c]thiadiazines, originating from triazole derivatives, thiadiazine derivatives, or thiocarbohydrazide. The triazolothiadiazine derivatives exhibit several biological actions, including antibacterial, anticancer, antiviral, antiproliferative, analgesic, anti-inflammatory, and antioxidant properties. The review article aims to assist researchers in creating new biologically active compounds for designing target-oriented triazolothiadiazine-based medicines to treat multifunctional disorders.

Keywords: biological activity; thiadiazine; thiocarbohydrazide; triazolo[3,4-b]thiadiazines; triazolo[4,3-c]thiadiazines triazol; triazolo[5,1-b]thiadiazines.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
Isomeric forms of triazolothiadiazine.
Figure 2
Figure 2
Synthetic methodologies involving triazolothiadiazines.
Scheme 1
Scheme 1
Synthesis of -[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines 3A [6], 3B [9], and 3C [23].
Scheme 2
Scheme 2
Synthesis of [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines 7A and 7B.
Scheme 3
Scheme 3
Synthesis of -[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines 8 and 9.
Scheme 4
Scheme 4
Synthesis of bis(1,2,4-triazolo[3,4-b][1,3,4]thiadiazine) derivatives 11.
Scheme 4
Scheme 4
Synthesis of bis(1,2,4-triazolo[3,4-b][1,3,4]thiadiazine) derivatives 11.
Scheme 5
Scheme 5
Synthesis triazolothiadiazine derivatives 12–14.
Scheme 6
Scheme 6
Synthesis of triazolo[3,4-b]thiadiazines derivatives 15 and 16.
Scheme 7
Scheme 7
Synthesis of 6,7-diphenyl-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine derivatives 18a,b.
Scheme 8
Scheme 8
Synthesis of triazolo[3,4-b][1,3,4]thiadiazine derivatives 19, 20, 21, and 22.
Scheme 9
Scheme 9
Synthesis of triazolothiadiazines 23a–l.
Scheme 10
Scheme 10
Mechanism of formation of triazolothiadiazines 23a–l.
Scheme 11
Scheme 11
Synthesis of triazolo[3,4-b][1,3,4]thiadiazines 31.
Scheme 12
Scheme 12
Synthesis of [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines 36.
Scheme 13
Scheme 13
Synthesis of 7-aroyl-6-methyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines 38.
Scheme 14
Scheme 14
Mechanism of formation of triazolothiadiazines 38.
Scheme 15
Scheme 15
Synthesis of [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines 45.
Scheme 16
Scheme 16
The mechanism of formation [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines 45.
Scheme 17
Scheme 17
Synthesis of triazolothiadiazines 49a–g.
Scheme 18
Scheme 18
Synthesis of triazolothiadiazines 50 and 51.
Scheme 19
Scheme 19
Synthesis of benzimidazole-triazolothiadiazine derivatives 52a–p.
Scheme 20
Scheme 20
Synthesis of 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines 53a–j.
Scheme 21
Scheme 21
Synthesis of 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines 54 [37,38,39,40,41,42,43,44,45,46,47,48,49].
Scheme 21
Scheme 21
Synthesis of 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines 54 [37,38,39,40,41,42,43,44,45,46,47,48,49].
Scheme 22
Scheme 22
Synthesis of long chain triazolothiadiazines 55a–d.
Scheme 23
Scheme 23
Synthesis of triazolothiadiazine derivatives 56.
Scheme 24
Scheme 24
Synthesis of 1-Aryl-2-((6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)thio)ethan-1-ones 57a–p.
Scheme 25
Scheme 25
Synthesis of triazolo[3,4-b]thiadiazines 58 and 59.
Scheme 26
Scheme 26
Synthesis of triazolothiadiazines 60 and 61.
Scheme 27
Scheme 27
Mechanism of formation of triazolothiadiazines 60 and 61.
Scheme 28
Scheme 28
Synthesis of triazolo[3,4-b][1,3,4]thiadiazinyl methanones 64.
Scheme 29
Scheme 29
Synthesis of fused heterocycle triazolothiadiazines 66 and 67.
Scheme 30
Scheme 30
Synthesis of triazolothiadiazinyl pyrazol-3-one derivatives 70.
Scheme 31
Scheme 31
Synthesis of triazolo[3,4-b]thiadiazines 71 and 72.
Scheme 32
Scheme 32
Synthesis of triazolothiadiazinyl dihydrophthalazine-1,4-diones 74 and triazolothiadiazine hydrazone 75.
Scheme 33
Scheme 33
Synthesis of triazolothiadiazine hydrazone derivatives 76.
Scheme 34
Scheme 34
Synthesis of triazolothiadiazine hydrazone derivatives 77.
Scheme 35
Scheme 35
Mechanism of formation of hydrazone derivatives 77.
Scheme 36
Scheme 36
Synthesis of 3-pyrazolyl triazolothiadiazines 82.
Scheme 37
Scheme 37
Synthesis of triazolo thiadiazinyl coumarins 87.
Scheme 38
Scheme 38
Synthesis of 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines 89a–i.
Scheme 39
Scheme 39
Synthesis of pyrimido[4,5-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazines 91a–g.
Scheme 40
Scheme 40
Mechanism of formation of triazolothiadiazines 91a–g.
Scheme 41
Scheme 41
Synthesis of triazolothiadiazines 96a–l.
Scheme 42
Scheme 42
Synthesis of triazolo[5,1-b]thiadiazine-3-carboxylates 98a–k.
Scheme 43
Scheme 43
Synthesis of [1,2,4]triazolo[5,1-b][1,3,5]thiadiazines 99a–l.
Scheme 44
Scheme 44
Synthesis of triazolo[4,3-c]thiadiazine-5-thiones 101 and triazolo[4,3-c]thiadiazin-5-imines 102.
Scheme 45
Scheme 45
Synthesis of 3,5-dihydro-7H-[1,2,4]triazolo[1,5-c][1,3,5]thiadiazine 6,6-dioxides 104.
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