Abstract:The synthesis of a series of isoelectronic analogues of (S)-2-[3-(tert-butylamino)-2-hydroxypropoxy]-3-cyanopyridine (1) are described; included in this group are examples of thiazole, isothiazole, thiadiazole, pyrazine, and the structurally related naphthyridines. All of the compounds are similar to 1 in that they contain a cyano group ortho to the aminohydroxypropoxy side chain and meta to the nitrogen heteroatom. In addition, several related examples, having additional nuclear substituents and/or groups oth… Show more
“…The solid separated out was filtered, washed thoroughly with water and crystallized from ethanol (Scheme 1). Synthesis of 5H- [1,2,4]triazolo [3,4-b] [1,3,4] thiadiazines (4a-o) A mixture of compound 3 (10 mmol), catalytic amount of hydrazine hydrate (1 mmol) and DMF (5 mL) as an energy transfer medium was exposed to microwave irradiations for 30 seconds. After that β-diketone/ β-ketoester (10 mmol) was added to the reaction mixture and again exposed to microwave irradiations intermittently at 30 seconds for three minutes.…”
Section: Microwave Irradiation Methodsmentioning
confidence: 99%
“…All data were found in accordance with the proposed structures of synthesized compounds. All the 5H- [1,2,4]triazolo [3,4-b] [1,3,4]thiadiazine derivatives (4a-o) along with some standard antibiotics and antifungal drugs were screened for their antimicrobial activities against selected bacteria and fungus. All the antimicrobial activity results are summarized in Table 1.…”
Section: Methodsmentioning
confidence: 99%
“…The yield obtained from microwave methods was better as compared to conventional method. The target compounds, 5H- [1,2,4]triazolo [3,4-b] [1,3,4]thiadiazine derivatives (4a-o) were prepared by environmental friendly method (Scheme 2) in which the mixture of intermediate compound 3, β-diketone / β-ketoester and catalytic amount of hydrazine hydrate irradiated in microwave oven. The purity of the compounds was checked by TLC.…”
Section: Methodsmentioning
confidence: 99%
“…In general, biological active compounds are derived from heterocyclic structures. Heterocycles containing 1,2,4-triazole and 1,3,4-thiadiazine nucleus have been well studied for a number of pathological conditions including inflammation 1,2 , hypertension 3 and aching 4 . The 1,3,4-thiadiaznie derivatives in which 1,4-thiazines fused with 1,2,4-triazole nucleus are important scaffold in several natural and synthetic compounds of significant pharmacological properties and also have structural similarity with biologically most active phenothiazines in having fold along N-S axis 5 .…”
Structurally diverse new series of 5H-[1,2,4]triazolo [3,4b] [1,3,4]thiadiazine heterocycles having medicinally privileged nucleus have been synthesized by simple and solvent free environmental benign methods. A mixture of 4-amino-5-substituted-1,2,4-triazolo-3-thiol and β-diketone/ β-ketoester and catalytic amount of hydrazine hydrate exposed to microwave irradiation in microwave oven. The intermediate 4-amino-1,2,4-triazole-3-thiols were also synthesized by entirely new solvent free environmental friendly methods. The synthesized target compounds (4a-o) were characterized by elemental analysis as well as spectral studies and screened for antimicrobial activities.
“…The solid separated out was filtered, washed thoroughly with water and crystallized from ethanol (Scheme 1). Synthesis of 5H- [1,2,4]triazolo [3,4-b] [1,3,4] thiadiazines (4a-o) A mixture of compound 3 (10 mmol), catalytic amount of hydrazine hydrate (1 mmol) and DMF (5 mL) as an energy transfer medium was exposed to microwave irradiations for 30 seconds. After that β-diketone/ β-ketoester (10 mmol) was added to the reaction mixture and again exposed to microwave irradiations intermittently at 30 seconds for three minutes.…”
Section: Microwave Irradiation Methodsmentioning
confidence: 99%
“…All data were found in accordance with the proposed structures of synthesized compounds. All the 5H- [1,2,4]triazolo [3,4-b] [1,3,4]thiadiazine derivatives (4a-o) along with some standard antibiotics and antifungal drugs were screened for their antimicrobial activities against selected bacteria and fungus. All the antimicrobial activity results are summarized in Table 1.…”
Section: Methodsmentioning
confidence: 99%
“…The yield obtained from microwave methods was better as compared to conventional method. The target compounds, 5H- [1,2,4]triazolo [3,4-b] [1,3,4]thiadiazine derivatives (4a-o) were prepared by environmental friendly method (Scheme 2) in which the mixture of intermediate compound 3, β-diketone / β-ketoester and catalytic amount of hydrazine hydrate irradiated in microwave oven. The purity of the compounds was checked by TLC.…”
Section: Methodsmentioning
confidence: 99%
“…In general, biological active compounds are derived from heterocyclic structures. Heterocycles containing 1,2,4-triazole and 1,3,4-thiadiazine nucleus have been well studied for a number of pathological conditions including inflammation 1,2 , hypertension 3 and aching 4 . The 1,3,4-thiadiaznie derivatives in which 1,4-thiazines fused with 1,2,4-triazole nucleus are important scaffold in several natural and synthetic compounds of significant pharmacological properties and also have structural similarity with biologically most active phenothiazines in having fold along N-S axis 5 .…”
Structurally diverse new series of 5H-[1,2,4]triazolo [3,4b] [1,3,4]thiadiazine heterocycles having medicinally privileged nucleus have been synthesized by simple and solvent free environmental benign methods. A mixture of 4-amino-5-substituted-1,2,4-triazolo-3-thiol and β-diketone/ β-ketoester and catalytic amount of hydrazine hydrate exposed to microwave irradiation in microwave oven. The intermediate 4-amino-1,2,4-triazole-3-thiols were also synthesized by entirely new solvent free environmental friendly methods. The synthesized target compounds (4a-o) were characterized by elemental analysis as well as spectral studies and screened for antimicrobial activities.
“…Many naturally occurring as well as synthetic compounds containing the pyridine scaffold exhibit interesting pharmacological properties [6][7][8][9][10]. Furthermore, pyridine is one of the most popular N-heteroaromatics incorporated into the structure of many pharmaceuticals.…”
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