273-84-7

Usage

Uses

Used in Pharmaceutical Industry:
[1,3]Thiazolo[5,4-b]pyridine is used as a pharmaceutical agent for its potential antiviral and antibacterial properties, offering a new avenue for the development of treatments against various infectious diseases.
Used in Agrochemical Industry:
In the agrochemical sector, [1,3]Thiazolo[5,4-b]pyridine is utilized as a component in the development of pesticides and other agrochemical products, potentially enhancing crop protection and yield.
Used in Organic Synthesis:
[1,3]Thiazolo[5,4-b]pyridine serves as a building block in organic synthesis, allowing for the creation of new compounds with a range of desirable properties, which can be applied across various industries, including but not limited to pharmaceuticals and materials science.
Used in Medicinal Chemistry Research:
[1,3]Thiazolo[5,4-b]pyridine is employed in medicinal chemistry research as a target for the discovery and development of new drugs, given its unique structure and biological activity potential, which could lead to innovative therapeutic agents.

Synthetic route

2-Chloro-3-nitropyridine (5470-18-8) + thiocarboxamide (115-08-2) → [1,3]thiazolo[5,4-b]pyridine (273-84-7)

Conditions	Yield
In sulfolane at 135℃; Microwave irradiation;	26%

thiazolo[5,4-b]pyridine-2-carboxylic acid (857969-93-8) → [1,3]thiazolo[5,4-b]pyridine (273-84-7)

Conditions	Yield
at 160 - 175℃;

2-methylthiazolo[5,4-b]pyridine (91813-40-0) → [1,3]thiazolo[5,4-b]pyridine (273-84-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous KMnO4 2: 160 - 175 °C View Scheme

2-Chloro-3-nitropyridine (5470-18-8) → [1,3]thiazolo[5,4-b]pyridine (273-84-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium disulfide 2: zinc-powder; acetic acid anhydride; acetic acid 3: aqueous KMnO4 4: 160 - 175 °C View Scheme

3,3’-dinitro-2,2’-dipyridinyl disulfide (4282-19-3) → [1,3]thiazolo[5,4-b]pyridine (273-84-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: zinc-powder; acetic acid anhydride; acetic acid 2: aqueous KMnO4 3: 160 - 175 °C View Scheme

[1,3]thiazolo[5,4-b]pyridine (273-84-7) + N-(((E)-2-chlorophenyl)methylidene)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide → N-((2-chlorophenyl)([1,3]thiazolo[5,4-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide (1402598-55-3)

Conditions	Yield
Stage #1: [1,3]thiazolo[5,4-b]pyridine With n-butyllithium In tetrahydrofuran; toluene at -78℃; for 0.166667h; Stage #2: N-(((E)-2-chlorophenyl)methylidene)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide In tetrahydrofuran; toluene for 0.166667h;	15%

[1,3]thiazolo[5,4-b]pyridine (273-84-7) → 2-mercapto-3-amino pyridine (38240-21-0)

Conditions	Yield
With hydrazine hydrate Ambient temperature;

[1,3]thiazolo[5,4-b]pyridine (273-84-7) + 1-(2-chlorophenyl)-4-iodo-5-methyl-1H-[1,2,3]triazole (864867-07-2) → 4-(thiazolo[5,4-b]pyridine-2-yl)-1-(2-chlorophenyl)-5-methyl-1H-[1,2,3]triazole

Conditions	Yield
With sodium acetate; trans-di-µ-acetatebis[2-(di-o-tolylphosphino)benzyl]dipalladium (II) In N,N-dimethyl-formamide at 140℃; for 8h;

[1,3]thiazolo[5,4-b]pyridine (273-84-7) + N-((2-(methylsulfanyl)phenyl)methylidene)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide (1402599-44-3) → N-((2-(methylsulfanyl)phenyl)([1,3]thiazolo[5,4-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide (1402607-94-6)

Conditions	Yield
Stage #1: [1,3]thiazolo[5,4-b]pyridine With n-butyllithium In tetrahydrofuran; toluene at -78℃; for 0.25h; Stage #2: N-((2-(methylsulfanyl)phenyl)methylidene)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide In tetrahydrofuran; toluene for 0.166667h;

[1,3]thiazolo[5,4-b]pyridine (273-84-7) + N-((2-methoxyphenyl)methylidene)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide (1402599-45-4) → N-((2-methoxyphenyl)([1,3]thiazolo[5,4-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide (1402598-52-0)

Conditions	Yield
Stage #1: [1,3]thiazolo[5,4-b]pyridine With n-butyllithium In tetrahydrofuran; toluene at -78℃; for 0.25h; Stage #2: N-((2-methoxyphenyl)methylidene)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide In tetrahydrofuran; toluene for 0.166667h;

[1,3]thiazolo[5,4-b]pyridine (273-84-7) + N-((2-chlorophenyl)methylidene)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide (1402599-46-5) → N-((2-chlorophenyl)([1,3]thiazolo[5,4-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide (1402598-55-3)

Conditions	Yield
Stage #1: [1,3]thiazolo[5,4-b]pyridine With n-butyllithium In tetrahydrofuran; toluene at -78℃; for 0.166667h; Stage #2: N-((2-chlorophenyl)methylidene)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide In tetrahydrofuran; toluene for 0.166667h;

[1,3]thiazolo[5,4-b]pyridine (273-84-7) + N-((3-methoxy-2-pyridinyl)methylidene)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide (1402599-47-6) → N-((3-methoxy-2-pyridinyl)([1,3]thiazolo[5,4-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide (1402598-58-6)

Conditions	Yield
Stage #1: [1,3]thiazolo[5,4-b]pyridine With n-butyllithium In tetrahydrofuran; toluene at -78℃; for 0.25h; Stage #2: N-((3-methoxy-2-pyridinyl)methylidene)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide In tetrahydrofuran; toluene for 6h;

Upstream product

• 857969-93-8 thiazolo[5,4-b]pyridine-2-carboxylic acid 
• 5470-18-8 2-Chloro-3-nitropyridine 
• 115-08-2 thiocarboxamide 
• 4282-19-3 3,3’-dinitro-2,2’-dipyridinyl disulfide 
• 91813-40-0 2-methylthiazolo[5,4-b]pyridine 

Downstream Products

• 38240-21-0 2-mercapto-3-amino pyridine 
• 1402607-94-6 N-((2-(methylsulfanyl)phenyl)([1,3]thiazolo[5,4-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide 
• 1402598-52-0 N-((2-methoxyphenyl)([1,3]thiazolo[5,4-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide 
• 1402598-55-3 N-((2-chlorophenyl)([1,3]thiazolo[5,4-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide 

Relevant academic research and scientific papers

A single-step preparation of thiazolo[5,4-b]pyridine- and thiazolo[5,4-c]pyridine derivatives from chloronitropyridines and thioamides, or thioureas

(Chemical Equation Presented) A one-step synthesis of thiazolo[5,4-b] pyridines from an appropriately substituted chloronitropyridine and thioamide, or thiourea, is presented. In particular, the reaction was used to prepare a large number of 6-nitrothiazo

Thiazolo [4,5-6] pyridine derivatives and anti-ulcerative composition containing same

Compounds of the general formula (I): STR1 and pharmaceutically acceptable salts thereof, in which A, B, C and D each represent --CH= or --N=, with the proviso that at least one of them is --N=; X represents --NH--, --O-- or --S--; Y represents --(CH2)p -- wherein p is an integer from 0 to 4, --C(CH3)2 --, --CH2 CH=CH--, --CH2 CO--, --CF2 -- or --CH2 COCH2 --; R1 represents a hydrogen atom, a C1-4 alkyl group, a halogen atom or a C1-4 alkoxy group; R2 represents a hydrogen atom, a hydroxyl group, a saturated or unsaturated C1-6 alkyl group, a C1-6 alkoxy group, a carboxyl group, a saturated or unsaturated C1-12 alkoxycarbonyl group which may be optionally substituted, a cycloalkoxycarbonyl group, a saturated or unsaturated five- or six-membered heterocyclic group containing at least one nitrogen atom optionally with one or more nitrogen and/or oxygen atoms, which may be optionally condensed and/or substituted, --CONR3 R4, --NR3 R4, --OCOR3 or --NHCONHR3 wherein R3 and R4, which may be the same or different, represent a C1-6 alkyl group which may be optionally substituted or a cycloalkyl group, and m and n each represent an integer from 0 to 2.