251-56-9

Usage

Uses

Used in Organic Synthesis:
Thiazolo[5,4-d]thiazole serves as a key building block in the synthesis of various organic compounds due to its reactive and stable nature, contributing to the development of novel chemical entities with potential applications across different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, Thiazolo[5,4-d]thiazole is utilized as a core structure in the design and synthesis of new drug molecules, leveraging its unique chemical properties to enhance drug efficacy and target specific biological pathways.
Used in Organic Electronic Devices:
Thiazolo[5,4-d]thiazole has been studied for its potential in organic electronic devices such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells, where its electronic properties can be harnessed to improve device performance and efficiency.
Used in Antimicrobial Applications:
Derivatives of Thiazolo[5,4-d]thiazole have demonstrated promising antimicrobial activities, making them valuable candidates for the development of new antimicrobial agents to combat drug-resistant infections.
Used in Antitumor Applications:
Thiazolo[5,4-d]thiazole derivatives have shown potential antitumor activities, indicating their use in the development of novel anticancer drugs that could target and inhibit tumor growth.
Used in Antiviral Applications:
The antiviral properties of Thiazolo[5,4-d]thiazole derivatives have been recognized, suggesting their potential use in creating new antiviral medications to treat viral infections and diseases.

Synthetic route

thiazolo<5,4-d>thiazole-2,5-dicarboxylic acid (27492-59-7) → thiazolo[5,4-d]thiazole (251-56-9)

Conditions	Yield
With ethanol for 24h; Heating;	79%
at 225 - 230℃; under 5 Torr;
In ethanol at 80℃; for 48h;

diethyl thiazolo[5,4-d]thiazole-2,5-dicarboxylate (27484-49-7) → thiazolo[5,4-d]thiazole (251-56-9)

Conditions	Yield
With potassium hydroxide In ethanol for 8h; Heating;	75%

2,5-dichlorothiazolo[5,4-d]thiazole (50616-95-0) → thiazolo[5,4-d]thiazole (251-56-9)

Conditions	Yield
With acetic acid; zinc for 9h; Heating;	52%

p-trifluoromethylphenyl bromide (402-43-7) + thiazolo[5,4-d]thiazole (251-56-9) → 2,5-bis(4-trifluoromethylphenyl)-1,3-thiazolo[5,4-d]-1,3-thiazole

Conditions	Yield
With copper diacetate; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 135℃; for 18h; Inert atmosphere;	65%

thiazolo[5,4-d]thiazole (251-56-9) → 2,5-dibromothiazolo[5,4-d]thiazole (1040390-19-9)

Conditions	Yield
With pyridine In tetrachloromethane for 4h; Heating;	58%
With pyridine; bromine In tetrachloromethane at 80℃; for 4h;	45%

thiazolo[5,4-d]thiazole (251-56-9) → 2-chlorothiazolo[5,4-d]thiazole (1040390-17-7) + 2,5-dichlorothiazolo[5,4-d]thiazole (50616-95-0)

Conditions	Yield
With trichloroisocyanuric acid In tetrachloromethane for 168h; Heating;	A 40% B 44%

thiazolo[5,4-d]thiazole (251-56-9) → 2-bromothiazolo[5,4-d]thiazole (1040390-18-8) + 2,5-dibromothiazolo[5,4-d]thiazole (1040390-19-9)

Conditions	Yield
With pyridine; bromine In tetrachloromethane for 4h; Heating;	A 35% B 14%

carbon dioxide (124-38-9) + thiazolo[5,4-d]thiazole (251-56-9) → thiazolo[5,4-d]thiazole-2-carboxylic acid (27484-58-8)

Conditions	Yield
(i) BuLi, (ii)/BRN= 1900390/; Multistep reaction;

Upstream product

• 27492-59-7 thiazolo<5,4-d>thiazole-2,5-dicarboxylic acid 
• 27484-49-7 diethyl thiazolo[5,4-d]thiazole-2,5-dicarboxylate 
• 50616-95-0 2,5-dichlorothiazolo[5,4-d]thiazole 

Downstream Products

• 1040390-18-8 2-bromothiazolo[5,4-d]thiazole 
• 1040390-19-9 2,5-dibromothiazolo[5,4-d]thiazole 

Relevant academic research and scientific papers

HETEROARYL COMPOUNDS FOR TREATING HUNTINGTON'S DISEASE

The present description relates to compounds, forms, and pharmaceutical compositions thereof and methods of using such compounds, forms, or compositions thereof for treating or ameliorating Huntington's disease. In particular, the present description relates to substituted bicyclic heteroaryl compounds of Formula (I), Formula (II), Formula (III), or Formula (IV), forms and pharmaceutical compositions thereof and methods of using such compounds, forms, or compositions thereof for treating or ameliorating Huntington's disease.

Preparation of halogenated derivatives of thiazolo[5,4-d]thiazole via direct electrophilic aromatic substitution

(Chemical Equation Presented) Chlorination and bromination reactions of thiazolo[5,4-d]thiazole led to the generation of its mono- and dihalogenated derivatives. These are the first instances of successful direct electrophilic aromatic substitution in the thiazolo[5,4-d]thiazole ring system. X-ray analysis demonstrates that both 2-bromothiazolo[5,4-d]-thiazole and 2,5- dibromothiazolo[5,4-d]thiazole are planar structures, with strongly manifested π-stacking in the solid state. Theoretical analysis of the pyridine-catalyzed halogenation (MP2/6-31+G(d) and B3LYP/6-31+G(d) calculations) reveals that introduction of one halogen actually leads to a slightly enhanced reactivity towards further halogenation. Several halogenation mechanisms have been investigated: 1) The direct C-halogenation with N-halopyridine as electrophile; 2) C-halogenation via intermediate N-halogenation, and 3) C-halogenation following an addition - elimination pathway, with intermediate formation of a cyclic halonium ion. The theoretical studies suggest that the direct C-halogenation is the favored mechanism.

Improved access to thiazolo[5,4-d]thiazole and thieno[2,3-d]thiazole

Five-membered rings are of interest as building blocks for nonlinear optical (NLO) materials. We found easy access to the title compounds: thiazolo[5,4-d]thiazole 1 has been obtained in three simple steps starting with the chlorination of ethyl isothiocyanatoacetate 8, followed by dehydrohalogenation to the diethyl 2,5-dicarboxylate of 1, which yielded 1 after saponification and decarboxylation. Thieno[2,3-d]-thiazole 2 has been synthesized in two steps by reductive deamination of the easily available 2-aminothieno[2,3-d]thiazole 5.