Effective synthesis of 6-substituted 7H-tetrazolo[5,1-b][1,3,4]thiadiazines via a one-pot condensation/nitrosation/azide-tetrazole tautomerism reaction sequence

Epishina, Margarita A.; Ферштат, Леонид Л.; Romanova, Anna A.; Махова, Нина Н.

doi:10.1016/j.tetlet.2017.09.014

Cited by 15 publications

(2 citation statements)

References 63 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A series of hetarylfuroxans was synthesized through cyclocondensation of bromoacetylfuroxans 44 with various binucleophiles [ 87 , 88 , 89 ]. In particular, a regioselective condensation of substrates 44 with thiosemicarbazide afforded hydrazinylthiazoles 45 which underwent in situ reaction with aldehydes resulting in a formation of the corresponding hydrazones 46 ( Scheme 26 ).…”

Section: Furoxansmentioning

confidence: 99%

Recent Advances in the Synthesis and Biomedical Applications of Heterocyclic NO-Donors

Ферштат

Zhilin

2021

Molecules

Self Cite

View full text Add to dashboard Cite

Nitric oxide (NO) is a key signaling molecule that acts in various physiological processes such as cellular metabolism, vasodilation and transmission of nerve impulses. A wide number of vascular diseases as well as various immune and neurodegenerative disorders were found to be directly associated with a disruption of NO production in living organisms. These issues justify a constant search of novel NO-donors with improved pharmacokinetic profiles and prolonged action. In a series of known structural classes capable of NO release, heterocyclic NO-donors are of special importance due to their increased hydrolytic stability and low toxicity. It is no wonder that synthetic and biochemical investigations of heterocyclic NO-donors have emerged significantly in recent years. In this review, we summarized recent advances in the synthesis, reactivity and biomedical applications of promising heterocyclic NO-donors (furoxans, sydnone imines, pyridazine dioxides, azasydnones). The synthetic potential of each heterocyclic system along with biochemical mechanisms of action are emphasized.

show abstract

Section: Furoxansmentioning

confidence: 99%

Recent Advances in the Synthesis and Biomedical Applications of Heterocyclic NO-Donors

Ферштат

Zhilin

2021

Molecules

Self Cite

View full text Add to dashboard Cite

show abstract

“…Synthesis of 6‐furoxanyl‐7 H ‐tetrazolo[5,1‐ b ][1,3,4]thiadiazine ( 47 ) was achieved by one‐pot condensation of 4‐amino‐3‐(α‐bromoacetyl)furoxan ( 46 ) with 1 in dimethyl sulfoxide for 1 h. Nitrosation of the formed hydrazinyl‐1,3,4‐thiadiazine using NaNO 2 /HCl, and an intramolecular cyclization of the nitrosation product via azide‐tetrazole tautomerism yielded 47 in 85% yield (Scheme ) .…”

Section: Thiocarbohydrazidesmentioning

confidence: 99%

An Update of the Use of Thiocarbohydrazides and Thiosemicarbazides in the Preparation of Heterocycles and Their Biological Importance

Aly

Hassan

AbdEl‐latief

2018

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

The inherent reactivity of thiocarbohydrazides and thiosemicarbazides makes them valuable as building blocks for the synthesis of other heterocyclic motifs. This review article discusses the recent applications of classes of compounds in syntheses of five‐membered to seven‐membered heterocycles of biological activities and remarkable number of metal complexes. Many previous reviews dealt with the reactivity of either thiosemicarbazides or thiocarbohydrazides. However, a large number of publications have recently dealt with the reactivity of thiosemicarbazides and thiocarbohydrazides. Consequently, we have found that it is of importance to shed new light on these interesting molecules.

show abstract

Effective synthesis of 7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines

Epishina

Ферштат

Махова

2018

Chem Heterocycl Comp

View full text Add to dashboard Cite

Effective synthesis of 6-substituted 7H-tetrazolo[5,1-b][1,3,4]thiadiazines via a one-pot condensation/nitrosation/azide-tetrazole tautomerism reaction sequence

Cited by 15 publications

References 63 publications

Recent Advances in the Synthesis and Biomedical Applications of Heterocyclic NO-Donors

Recent Advances in the Synthesis and Biomedical Applications of Heterocyclic NO-Donors

An Update of the Use of Thiocarbohydrazides and Thiosemicarbazides in the Preparation of Heterocycles and Their Biological Importance

Effective synthesis of 7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines

Contact Info

Product

Resources

About