7305-71-7

Basic information

• Product Name: 2-Amino-5-methylthiazole
• Synonyms: 2-Amino-5-methylthiazole ,99%;Meloxicam Related Compound B (25 mg) (2-Amino-5-methyl-thiazole);2-Amino-5-methylthia;5-Methyl-1,3-thiazol-2-ylaMine;5-Methyl-2-aMinothiazole;NSC 523150;2-Amino-5-methyl-1,3-thiazole;Meloxicam EP Impurity B
• CAS NO: 7305-71-7
• Molecular Formula: C₄H₆N₂S
• Molecular Weight: 114.17
• EINECS: 423-800-5
• Product Categories: Heterocyclic Building Blocks;C3 to C7;Chemical Synthesis;Heterocyclic Building Blocks;Intermediates of Dyes and Pigments;Amines;blocks;Thiazoles;Sulphur Derivatives;INTERMEDIATESOFMELOXICAN;Thiazoles, Isothiazoles &Benzothiazoles;Amino;Building Blocks;Pyrimidine;Organohalides;Thiazoles, Isothiazoles & Benzothiazoles;Building Blocks;2-Amino-5-Methylthiazole sky;18031153937@189.cn
• Mol File: 7305-71-7.mol
• Article Data: 16

Chemical Properties

• Melting Point: 93-98 °C(lit.)
• Boiling Point: 232.5 °C at 760 mmHg
• Flash Point: 94.4 °C
• Appearance: Brown/Powder
• Density: 1.258 g/cm³
• Vapor Pressure: 0.0588mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 5.42±0.10(Predicted)
• BRN: 109603
• CAS DataBase Reference: 2-Amino-5-methylthiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-methylthiazole(7305-71-7)
• EPA Substance Registry System: 2-Amino-5-methylthiazole(7305-71-7)

Safety Data

• Hazard Codes: Xn,N,Xi
• Statements: 22-48/22-50/53-36/37/38
• Safety Statements: 60-61-29-26-37/39
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 7305-71-7(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 7305-71-7 differently. You can refer to the following data:
1. An aminothiazole derivative used in characterization and DNA-interaction studies via formation of metal complexes that bind competitively to DNA. 2-Amino-5-methylthiazole can be used in solar cells to influence the interaction with the TiO2 photoelectrode, which in turn alters the dye-sensitized solar cell performance.
2. 2-Amino-5-methylthiazole may be used in the preparation of acrylamide monomer, 5-methyl-2-thiozyl methacrylamide (MTMAAm).

General Description

2-Amino-5-methylthiazole is a heterocyclic building block. It is one of the major alkaline metabolite of tenoxicam (TX) and meloxicam (MX).

InChI:InChI=1/C4H6N2S/c1-3-2-6-4(5)7-3/h2H,1H3,(H2,5,6)

Synthetic route

methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (35511-15-0) + meloxicam (71125-38-7) → 5-methyl-2-thiazol-2-amine (7305-71-7)

Conditions	Yield
With montmorillonite MK10 impregnated with ZnCl2 In o-xylene for 24h; Reagent/catalyst; Reflux; Green chemistry;	90%

potassium thioacyanate + chloroacetone (78-95-5) → 5-methyl-2-thiazol-2-amine (7305-71-7)

Conditions	Yield
With ammonium acetate on neutral alumina; silica gel In benzene at 80℃; for 6h;	83%

1-isothiocyanatopropa-1,2-diene (137768-73-1) → 5-methyl-2-thiazol-2-amine (7305-71-7)

Conditions	Yield
With ammonia	59%
With ammonium hydroxide In tetrahydrofuran at 20℃; for 72h;	59%

1-isothiocyanatopropa-1,2-diene (137768-73-1) → 5-methyl-2-thiazol-2-amine (7305-71-7) + (5,5'-dimethyl-[2,3'-bithiazolyl]-2'-ylidene)-(5-methylthiazol-2-yl)-amine (137768-80-0) + 5,5'-dimethyl-2'-imino-[2,3'-bithiazolyl] (137768-81-1)

Conditions	Yield
With ammonium hydroxide In tetrahydrofuran at 20℃;	A 11% B 50% C n/a

propan-1-ol (71-23-8) → 5-methyl-2-thiazol-2-amine (7305-71-7)

Conditions	Yield
With chlorine at 8 - 10℃; Behandeln des Reaktionsprodukts mit Thioharnstoff;

propionaldehyde (123-38-6) + thiourea (17356-08-0) → 5-methyl-2-thiazol-2-amine (7305-71-7)

Conditions	Yield
With sulfuryl dichloride
With chloroform; bromine
With chloroform; iodine

2-chloropropanal (683-50-1) + thiourea (17356-08-0) → 5-methyl-2-thiazol-2-amine (7305-71-7)

bromo-2 propanal (19967-57-8) + thiourea (17356-08-0) → 5-methyl-2-thiazol-2-amine (7305-71-7)

Conditions	Yield
Reaktion des Hydrats;

thiourea (17356-08-0) + 2-bromopropionaldehyde diethyl acetal (3400-55-3) → 5-methyl-2-thiazol-2-amine (7305-71-7)

Conditions	Yield
With hydrogenchloride

thiourea (17356-08-0) + 2-bromo-propionaldehyde-hydrate → 5-methyl-2-thiazol-2-amine (7305-71-7)

phenyl N-2-(5-methylthiazolyl)carbamate (921203-76-1) → 5-methyl-2-thiazol-2-amine (7305-71-7) + phenol (108-95-2)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane at 25℃; Kinetics;

propionaldehyde (123-38-6) → 5-methyl-2-thiazol-2-amine (7305-71-7)

Conditions	Yield
With sulfuryl dichloride; thiourea In ethanol; chloroform
With sulfuryl dichloride; thiourea In ethanol; chloroform

2-(5-methylthiazol-2-yliminomethyl)phenol → 5-methyl-2-thiazol-2-amine (7305-71-7) + salicylaldehyde (90-02-8)

Conditions	Yield
With aluminium(III) chloride hexahydrate; water In methanol at 20℃; for 2h;

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-(((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)methyl)benzoic acid → 4-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)methyl)-N-(5-methylthiazol-2-yl)benzamide

Conditions	Yield
Stage #1: 4-(((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)methyl)benzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Stage #2: 5-methyl-2-thiazol-2-amine In N,N-dimethyl-formamide at 20℃;	98.61%
Stage #1: 4-(((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)methyl)benzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Stage #2: 5-methyl-2-thiazol-2-amine In N,N-dimethyl-formamide at 20℃;	98.61%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

5-methyl-2-thiazol-2-amine (7305-71-7) + 6-chloropyrazine-2-carboxylic acid chloride (148673-71-6) → 6-chloro-pyrazine-2-carboxylic acid (5-methyl-thiazol-2-yl)-amide

Conditions	Yield
With pyridine In acetone at 20℃; for 0.5h;	98%

5-methyl-2-thiazol-2-amine (7305-71-7) + 6-chloro-5-tert-butylpyrazine-2-carboxylic acid chloride (879131-25-6) → 5-tert-butyl-6-chloro-pyrazine-2-carboxylic acid (5-methyl-thiazol-2-yl)-amide

Conditions	Yield
With pyridine In acetone at 20℃; for 0.5h;	98%

5-methyl-2-thiazol-2-amine (7305-71-7) + ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (24683-26-9) → meloxicam (71125-38-7)

Conditions	Yield
In o-xylene for 24h; Product distribution / selectivity; Heating / reflux;	95%
In xylene at 139 - 140℃; for 32 - 37h; Product distribution / selectivity; Heating / reflux; Molecular sieve;	92.48%

5-methyl-2-thiazol-2-amine (7305-71-7) + 5-((4,6-dichloropyrimidin-2-yl)oxy)-4-fluoro-2-methyl-1H-indole (1609119-40-5) → N-(6-chloro-2-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)pyrimidin-4-yl)-5-methylthiazol-2-amine (1609119-46-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; sodium iodide In N,N-dimethyl-formamide at 70℃;	95%

5-methyl-2-thiazol-2-amine (7305-71-7) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → 1-(E)-[(5-methylthiazol-2-ylimino)methyl]naphthalen-2-ol

Conditions	Yield
In methanol for 6h; Reflux;	95%

5-methyl-2-thiazol-2-amine (7305-71-7) + cyanoacetic acid (372-09-8) → 2-cyano-N-(5-methylthiazol-2-yl)acetamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;	95%

5-methyl-2-thiazol-2-amine (7305-71-7) + 1,3-thiazole-2-carbonyl chloride (30216-57-0) → N-(2-methylthiazole-5-yl)-thiazole-2-carboxamide (475637-27-5)

Conditions	Yield
With triethylamine; lithium chloride In 1-methyl-pyrrolidin-2-one at 20℃; for 72h;	94%

5-methyl-2-thiazol-2-amine (7305-71-7) + 2-nitrobenzyl chloride (610-14-0) → N-(5-methylthiazol-2-yl)-2-nitrobenzamide

Conditions	Yield
In dichloromethane at 0℃; Inert atmosphere;	94%

5-methyl-2-thiazol-2-amine (7305-71-7) + acetyl chloride (75-36-5) → N-(5-methylthiazol-2-yl)acetamide (61996-32-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃; for 2h;	94%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃;

4-methyl-[1,2,3]thiadiazole-5-carbonyl chloride (59944-65-9) + 5-methyl-2-thiazol-2-amine (7305-71-7) → 4-methyl-N-(5'-methyl-1,3-thiazol-2'-yl)-1,2,3-thiadiazole-5-carboxamide

Conditions	Yield
In toluene at 100 - 105℃; for 4h; Solvent; Temperature; Reflux;	94%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + 4-chlorobenzaldehyde (104-88-1) → 7-(4-chlorophenyl)-10-methyl-6H,7H-chromeno[4,3-d]thiazolo[3,2-a]pyrimidin-6-one

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; 4-chlorobenzaldehyde at 20℃; Knoevenagel Condensation; Green chemistry; Stage #2: 5-methyl-2-thiazol-2-amine for 0.5h; Catalytic behavior; Temperature; Solvent; Reagent/catalyst; Reflux; Green chemistry;	94%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + 3,4 difluorobenzaldehyde (34036-07-2) → C20H12F2N2O2S

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; 3,4 difluorobenzaldehyde at 20℃; Knoevenagel Condensation; Green chemistry; Stage #2: 5-methyl-2-thiazol-2-amine for 0.583333h; Reflux; Green chemistry;	94%

5-methyl-2-thiazol-2-amine (7305-71-7) + Pyridine-2,6-dicarboxylic acid (499-83-2) → N2,N6-bis(5-methylthiazol-2-yl)pyridine-2,6-dicarboxamide

Conditions	Yield
Stage #1: 5-methyl-2-thiazol-2-amine; Pyridine-2,6-dicarboxylic acid With pyridine at 120℃; for 0.5h; Stage #2: With triphenyl phosphite at 100 - 120℃; for 6h;	94%

5-methyl-2-thiazol-2-amine (7305-71-7) → 2-chloro-5-methyl-thiazole (33342-65-3)

Conditions	Yield
With t-butyl thionitrite; copper dichloride In acetonitrile at 25℃; for 2.66667h; Inert atmosphere;	93%
With t-butyl thionitrite; copper dichloride In acetonitrile at 25℃; for 2.66667h; Time; Inert atmosphere;	93%
With 2-methylchlorobenzene; copper(l) chloride In hexane at 6 - 65℃; for 15h; Temperature;	81%

5-methyl-2-thiazol-2-amine (7305-71-7) + 2-chloro-6-fluorobenzoic acid (434-75-3) → 6-fluoro-2-methyl-5H-[1,3]-thiazolo[2,3-b]quinazolin-5-one

Conditions	Yield
With copper; potassium carbonate In N,N-dimethyl-formamide at 25℃; for 0.25h; sonication;	93%
With copper Ullmann condensation; Sonication;

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-(3-chloro-4-cyanophenoxy)butanoic acid → 4-(3-chloro-4-cyanophenoxy)-N-(5-methylthiazol-2-yl)butanamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 45℃; for 16h;	93%

5-methyl-2-thiazol-2-amine (7305-71-7) + m-nitrobenzoic acid chloride (121-90-4) → N-(5-methylthiazol-2-yl)-3-nitrobenzamide

Conditions	Yield
In dichloromethane at 0℃; Inert atmosphere;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 1-halo-2,4-dinitrobenzene → C10H8N4O4S

Conditions	Yield
With tributyl-amine In N,N-dimethyl-formamide at 100℃; for 12h; Flow reactor;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + benzaldehyde (100-52-7) → C20H14N2O2S

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; benzaldehyde at 20℃; Knoevenagel Condensation; Green chemistry; Stage #2: 5-methyl-2-thiazol-2-amine for 0.5h; Reflux; Green chemistry;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + 2-chloro-benzaldehyde (89-98-5) → C20H13ClN2O2S

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; 2-chloro-benzaldehyde at 20℃; Knoevenagel Condensation; Green chemistry; Stage #2: 5-methyl-2-thiazol-2-amine for 0.583333h; Reflux; Green chemistry;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + 3-Chlorobenzaldehyde (587-04-2) → C20H13ClN2O2S

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; m-Chlorobenzaldehyde at 20℃; Knoevenagel Condensation; Green chemistry; Stage #2: 5-methyl-2-thiazol-2-amine for 0.5h; Reflux; Green chemistry;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + m-bromobenzoic aldehyde (3132-99-8) → C20H13BrN2O2S

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; m-bromobenzoic aldehyde at 20℃; Knoevenagel Condensation; Green chemistry; Stage #2: 5-methyl-2-thiazol-2-amine for 0.633333h; Reflux; Green chemistry;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + 4-methyl-benzaldehyde (104-87-0) → C21H16N2O2S

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; 4-methyl-benzaldehyde at 20℃; Knoevenagel Condensation; Green chemistry; Stage #2: 5-methyl-2-thiazol-2-amine for 0.5h; Reflux; Green chemistry;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + 4-fluorobenzaldehyde (459-57-4) → C20H13FN2O2S

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; 4-fluorobenzaldehyde at 20℃; Knoevenagel Condensation; Green chemistry; Stage #2: 5-methyl-2-thiazol-2-amine for 0.75h; Reflux; Green chemistry;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-(4-chloro-3-methylphenoxy)-2-methylbutanoic acid → 4-(4-chloro-3-methylphenoxy)-2-methyl-N-(5-methylthiazol-2-yl)butanamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 45℃; for 16h;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 3,4-dichloro-isothiazole-5-carbonyl chloride (56914-82-0) → C8H5Cl2N3OS2

Conditions	Yield
Stage #1: 5-methyl-2-thiazol-2-amine With triethylamine In dichloromethane for 0.166667h; Cooling with ice; Stage #2: 3,4-dichloro-isothiazole-5-carbonyl chloride In dichloromethane at 20℃; for 3h;	91.6%

succinic acid anhydride (108-30-5) + 5-methyl-2-thiazol-2-amine (7305-71-7) → C8H10N2O3S (888125-33-5)

Conditions	Yield
In ethyl acetate at 20℃; for 2h;	91.3%
In tetrahydrofuran at 65℃; for 3h;

5-methyl-2-thiazol-2-amine (7305-71-7) + phthalic anhydride (85-44-9) → 2-(5-methyl-thiazol-2-yl)-isoindole-1,3-dione (832091-87-9)

Conditions	Yield
With triethylamine In toluene at 200℃; for 2h; Sealed tube;	91%
In 1,4-dioxane at 110℃;	56%

5-methyl-2-thiazol-2-amine (7305-71-7) + 1,3,5-trichloro-2,4,6-triazine (108-77-0) → C7H5Cl2N5S (1258205-29-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -5℃; Inert atmosphere;	91%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -5℃;	91%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -5℃;

Upstream product

• 71-23-8 propan-1-ol 
• 123-38-6 propionaldehyde 
• 17356-08-0 thiourea 
• 683-50-1 2-chloropropanal 
• 19967-57-8 bromo-2 propanal 
• 3400-55-3 2-bromopropionaldehyde diethyl acetal 
• 333-20-0 potassium thioacyanate 
• 78-95-5 chloroacetone 
• 137768-73-1 1-isothiocyanatopropa-1,2-diene 
• 35511-15-0 methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide 
• 71125-38-7 meloxicam 
• 921203-76-1 phenyl N-2-(5-methylthiazolyl)carbamate 

Downstream Products

• 13838-78-3 5-methyl-1,3-thiazole-2-carbaldehyde 
• 61996-32-5 N-(5-methylthiazol-2-yl)acetamide 
• 855230-93-2 4-nitro-N-5-methyl-thiazol-2-yl-benzenesulfonamide 
• 88614-86-2 N-acetyl-sulfanilic acid-(5-methyl-thiazol-2-ylamide) 
• 94579-97-2 4-acetylamino-N-[3-(4-acetylamino-benzenesulfonyl)-5-methyl-3H-thiazol-2-ylidene]-benzenesulfonamide 
• 13738-07-3 N-(5-methyl-thiazol-2-yl)-5-nitro-2-octyloxy-benzamide 
• 39122-64-0 Ethyl-N-(5-methylthiazol-2-yl)carbamat 
• 75793-02-1 2,5-dichloro-3,6-bis-(5-methyl-thiazol-2-ylamino)-[1,4]benzoquinone 
• 107518-43-4 2,5-dimethyl-6-phenyl-imidazo[2,1-b]thiazole 
• 39122-63-9 N-Ethoxycarbonyl-N'-(5-methylthiazol-2-yl)thioharnstoff 
• 51226-37-0 2-methyl-6-phenylimidazo<2,1-b>thiazole 
• 101717-13-9 2-methyl-5,6-diphenyl-imidazo[2,1-b]thiazole 
• 32187-00-1 2-methyl-5-oxo-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester 
• 92192-03-5 2-acetoxy-N-(5-methyl-thiazol-2-yl)-2-phenyl-acetamide 

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An innovative and efficient method to synthesize meloxicam in one-step procedure with respect to the green chemistry

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