248-02-2

Usage

Uses

Used in Organic Synthesis:
5,6-(1,3-Butadiene-1,4-diyl)thiazolo[3,2-d]tetrazole is used as a key intermediate in organic synthesis for the development of novel compounds with potential applications across various industries. Its unique structure allows for versatile chemical reactions, facilitating the creation of new molecules with desired properties.
Used in Materials Science:
In the field of materials science, 5,6-(1,3-Butadiene-1,4-diyl)thiazolo[3,2-d]tetrazole is utilized for its high thermal stability, making it a candidate for the development of advanced materials with improved performance characteristics under high-temperature conditions.
Used as an Energetic Material:
Due to its potential as an energetic material, 5,6-(1,3-Butadiene-1,4-diyl)thiazolo[3,2-d]tetrazole is explored for applications in propellants, explosives, and pyrotechnics. Its ability to release a significant amount of energy upon initiation makes it a valuable component in these high-energy-density materials.
Used in Drug Design and Development:
5,6-(1,3-Butadiene-1,4-diyl)thiazolo[3,2-d]tetrazole has shown potential as a pharmacophore for drug design and development. Its unique structure and properties make it a promising candidate for the creation of new pharmaceuticals, particularly in the area of medicinal chemistry where novel molecular scaffolds are constantly sought after for the treatment of various diseases.
Used in Biological Research:
5,6-(1,3-Butadiene-1,4-diyl)thiazolo[3,2-d]tetrazole has been studied for its potential biological activities, which may lead to its use in biological research for understanding its interactions with biological systems and its potential applications in therapeutics or as a research tool.

InChI:InChI=1/C7H4N4S/c1-2-4-6-5(3-1)11-7(12-6)8-9-10-11/h1-4H

Upstream product

• 136-95-8 2-amino-benzthiazole 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 615-21-4 1,3-benzothiazol-2-ylhydrazine 
• 941-55-9 4-toluenesulfonyl azide 
• 39582-59-7 benzothiazol-2-yl-lithium 
• 149-30-4 2-Mercaptobenzothiazole 
• 1123-99-5 2-iodobenzothiazole 

Downstream Products

• 30937-73-6 2-(3-phenyl-triazenyl)-benzothiazole 
• 23574-92-7 2-[3-(tris-dimethylamino-λ⁵-phosphanylidene)-triaz-1-enyl]-benzothiazole 
• 20415-66-1 N-(1,3-benzothiazol-2-yl)triphenyliminophosphorane 

Relevant academic research and scientific papers

Triazolbenzo[d]thiazoles: Efficient synthesis and biological evaluation as neuroprotective agents

A number of (1H-1,2,3-triazol-1-yl)benzo[d]thiazoles were synthesized utilizing a versatile Cu-catalyzed azide-alkyne click reaction (CuAAC) on tautomeric benzo[4,5]thiazolo[3,2-d]tetrazole (1) and 2-azidobenzo[d]thiazole (2) starting materials. Moreover, one of the resulting products of this investigation, triazolbenzo[d]thiazole 22, was found to possess significant neuroprotective activity in human neuroblastoma (SH-SY5Y) cells.

Development of benzothiazole 'click-on' fluorogenic dyes

'Click-on' fluorogenic reaction: a non-fluorescent benzothiazole with an electron-deficient alkyne group at 2-position reacts with azide containing molecules could form fluorescent adducts.

On the utility of the azido transfer protocol: Synthesis of 2- And 5-azido N-methylimidazoles, 1,3-thiazoles and N-methylpyrazole and their conversion to triazole - azole bisheteroaryls

The azido transfer procedure of heteroaryllithium and tosyl azide was used to synthesize selected 2- and 5-azidoazoles. This procedure, which is based on the fragmentation of the appropriate lithium triazene salts 1a-7a, successfully afforded 2-azido-N-methylimidazole 1, 2-azido-l,3-thiazole 2, 2-azidobenzo-1.3-thiazole 3, 5-azido-N-methylpyrazole 4, 5-azido-N- methylimidazole 6 [via 2-(trimethylsilyl)-5-azido-N-methylimidazole 5], and 5-azido-l,3-thiazole 7 (via 5-lithio-1,3-thiazole), but attempts to prepare 5-azido-2-(trimethylsilyl)-1,3-thiazole 8 from the corresponding triazene 7a failed, affording only the desilylated azide 7 in poor yield. Azidcs 1-7 underwent 1,3-dipolar cycloaddition when mixed with neat (trimethylsilyl) acetylene, giving 1-heteroaryl-4-trimethylsilyl-1,2.3-triazoles 1b-7b generally in very high yields. The Royal Society of Chemistry 2005.

Synthesis of New Condensed Pyrimidine Systems: Reactions of Heterocyclic Amines with Acetylenic Esters

Several hitherto unreported 1,3,4-oxa/thiadiazolopyrimidin-7-ones (1 and 2) and thiazolopyrimidin-7-ones (3) have been synthesised by the reaction of 2-amino-1,3,4-oxa/thiadiazoles and 2-amino-4-arylthiazoles respectively with ethyl phenylpropiolate.The reaction of these amines with diethyl acetylenedicarboxylate furnishes the 7-oxo-5-carbethoxy derivatives (8-10).A similar reaction of 2-aminobenzothiazole with diethyl acetylenedicarboxylate affords 4-carbethoxypyrimidobenzothiazol-2(H)-one (7).To assign the structures of the 7-oxo derivatives the isomeric 5-oxo-7-carbethoxy derivatives (14) have also been synthesised by an unambiguous route.

Studies on Heterocyclic Compounds. Part VI: Synthesis of Bridgehead Nitrogen Triazine and Pyrimidine Heterocycles

New bridgehead nitrogen containing heterocycles such as thiazolotriazine (IVa and IVb), imidazolotriazine (IVc), triazinotriazine (IVd and IVe) and oxadiazolotriazine (IVf) and several of their derivatives (V) have been prepared by reacting their respective hydrazine (II) with ethylpyruvate and phenyl glycoxalic acid.The diazotization of hydrazine (II) furnished the reactive intermediates (VI) (azido form) and (VII) (tetrazole form) depending on the structure of hydrazines.These intermediates have been used to synthesise bridgehead nitrogen pyrimidine derivatives (VIII) by reacting them with diethyl fumarate.The spectral and chemical evidences show that diazotised products obtained from 2-hydrazino-4-phenyl thiazole (IIa) and 2-hydrazino benzothiazole (IIb) exist in tetrazole form (VIIa) and (VIIb), respectively, whereas the remaining four (IIa-IIf) remain in the azido form (VIc-VIf) in the solid state.