58249-61-9

Usage

Uses

Used in Pharmaceutical Industry:
6-Benzothiazolecarbonitrie is used as a synthetic intermediate for the preparation of heteroaryl carboxylic acids and esters. These compounds are essential in the development of new drugs and pharmaceuticals, as they can be incorporated into the molecular structure of various therapeutic agents. The carboxylation of oxazoles, thiazoles, and oxadiazoles using 6-Benzothiazolecarbonitrie allows for the creation of diverse chemical structures with potential applications in medicine.
Used in Chemical Synthesis:
In the field of organic chemistry, 6-Benzothiazolecarbonitrie serves as a valuable reagent for the synthesis of various heterocyclic compounds. Its unique structure and reactivity make it a versatile building block for the creation of complex organic molecules, which can be further modified and functionalized to achieve desired properties and applications.
Used in Material Science:
6-BENZOTHIAZOLECARBONITRILE's ability to form stable complexes with other molecules makes it a potential candidate for use in the development of new materials with specific properties. For example, 6-Benzothiazolecarbonitrie can be used to create novel polymers, dyes, and pigments with unique characteristics, such as enhanced stability, color, or conductivity.

Upstream product

• 19759-66-1 2-amino-6-cyanobenzthiazole 
• 67-68-5 dimethyl sulfoxide 
• 33348-34-4 4-amino-3-iodobenzonitrile 
• 101084-51-9 benzothiazole-6-carboxamide 
• 873-74-5 4-Aminobenzonitrile 
• 107-13-1 acrylonitrile 
• 206662-96-6 4,5-bis(dibromomethyl)thiazole 
• 557-21-1 zinc(II) cyanide 
• 53218-26-1 6-bromo-1,3-benzothiazole 

Downstream Products

• 3622-35-3 benzothiazole-6-carboxylic acid 
• 174658-22-1 4-amino-3-mercaptobenzonitrile 
• 19759-66-1 2-amino-6-cyanobenzthiazole 
• 1421704-88-2 2-benzoylbenzo[d]thiazole-6-carbonitrile 
• 77333-68-7 2-phenylbenzo[d]thiazole-6-carbonitrile 

Relevant academic research and scientific papers

K2S as Sulfur Source and DMSO as Carbon Source for the Synthesis of 2-Unsubstituted Benzothiazoles

We describe a three-component reaction of o-iodoanilines with K2S and DMSO that provides 2-unsubstituted benzothiazoles in moderate to good isolated yields with good functional group tolerance. Electron-rich aromatic amines and o-phenylenediamines instead of o-iodoanilines provided 2-unsubstituted benzothiazoles and 2-unsubstituted benzimidazoles with and without K2S under similar conditions. Notably, DMSO plays three vital roles: carbon source, solvent, and oxidant.

Synthetic method of ammonium acetate-mediated benzothiazole compound

The invention discloses a synthetic method of an ammonium acetate-mediated benzothiazole compound . The synthetic method comprises the steps: adding an o-haloaniline derivative, potassium sulfide, dimethyl sulfoxide, a catalyst, an additive 1 and an additive 2 into a reaction tube, carrying out a stirring reaction at the temperature of 130-150 DEG C, cooling to room temperature after the reactionis finished, and separating and purifying the product to obtain the benzothiazole compound. The invention provides the synthetic method of the benzothiazole compound by taking K2S as a sulfur source,DMSO as a carbon source and an oxidizing agent, an o-haloaniline derivative as a substrate and an ammonium acetate mediated three-component one-pot method. The method has the advantages of fewer reaction steps, mild reaction conditions, good functional group tolerance and the like.

Method for synthesizing benzothiazole by microwave radiation of benzothioamide compound in aqueous phase

The invention discloses a method for synthesizing benzothiazole by microwave radiation of a benzothioamide compound in an aqueous phase. The method includes the steps: adding the benzothioamide compound into the aqueous phase under microwave conditions; performing cyclization under alkaline conditions to generate the benzothiazole. The method for preparing the benzothiazole is environmentally friendly, simple and convenient in operation, safe, cheap and efficient. Compared with the prior art, the method is applicable to a lot of functional groups, high in yield, few in by-products, simple in operation, safe, low in cost and environmentally friendly.

Mild palladium-catalyzed cyanation of (hetero)aryl halides and triflates in aqueous media

A mild, efficient, and low-temperature palladium-catalyzed cyanation of (hetero)aryl halides and triflates is reported. Previous palladium-catalyzed cyanations of (hetero)aryl halides have required higher temperatures to achieve good catalytic activity. This current reaction allows the cyanation of a general scope of (hetero)aryl halides and triflates at 2-5 mol % catalyst loadings with temperatures ranging from rt to 40 °C. This mild method was applied to the synthesis of lersivirine, a reverse transcriptase inhibitor.

Carbon dioxide as the C1 source for direct C-H functionalization of aromatic heterocycles

(Equation Presented). A simple and straightforward method has been developed for the direct carboxylation of aromatic heterocylces such as oxazoles, thiazoles, and oxadiazoles using CO2 as the C1 source. The reactions require no metal catalyst and only Cs2CO3 as the base. A good functional group tolerance is achieved.

HETERO COMPOUND

[Problems] To provide a useful compound as an active ingredient for a preventing and/or treating agent for rejection in the transplantation of an organ, bone marrow, or a tissue, an autoimmune disease, or the like, which has an excellent S1P1 a

Generation and Diels-Alder trapping of 4,5-bis(bromomethylene)-4,5-dihydrothiazole

Treatment of 4,5-bis(dlbromomethyl)thiazole (1a) with sodium iodide in DMF led to 4,5-bis(bromomethylene)-4,5-dihydrothiazole (2a). Trapping the latter in situ with dienophiles afforded directly the aromatized cycloadducts. Starting with 5-hydroxynaphthoquinone or its 2- and 3-bromo derivatives 6 gave a mixture of the tetracyclic quinones 10 + 11 from which the 1,6-regioisomer 10 predominates. Using acrylate dienophiles gave 6-substituted benzothiazoles 13 as the major products. The regiochemistry of the cycloadditions between 2a and naphthoquinones 6 agrees with the predictions of the frontier molecular orbital theory. In contrast, the regioselectivity observed from 2a and acrylate dienophiles 12, similar to that previously obtained with 5-bromomethylene-4-methylene-4,5-dihydrothiazole (2b), is opposite to that predicted and could be better accomodated by a competitive Michael addition followed by a cyclization-elimination step.

Synthesis and antifungal activity of novel thiazole-containing triazole antifungals. II. Optically active ER-30346 and its derivatives

A series of novel thiazole-containing triazole antifungals was synthesized and evaluated for antifungal activity against a variety of clinically isolated pathogenic fungi in vitro and against systemic candidosis in vivo. These compounds showed potent antifungal activities in vitro and in vivo. In particular, (2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-2-(2,4- difluorophenyl)-1-(1H-1,2,4-triazol-l-yl)-2-butanol (12g; ER-30346) showed potent and well-balanced in vitro activities and potent in vivo efficacy, and had a good safety profile.