156085-98-2

Upstream product

• 38421-66-8 N-(2-methoxyphenyl)benzothioamide 
• 5395-00-6 N-(2-methoxyphenyl)benzamide 
• 98-88-4 benzoyl chloride 

Downstream Products

• 94977-63-6 2-phenyl-4-hydroxybenzothiazole 

Relevant academic research and scientific papers

Method for preparing benzothiazole compound through microwave catalysis in water phase

The invention discloses a method for preparing a benzothiazole compound through/under microwave catalysis in a water phase. A water-soluble coordination compound is used as a catalyst, and a reactionof inorganic sulfide, 2-iodoaniline and aldehyde is efficiently catalyzed through microwaves in a pure water phase. The method for preparing the benzothiazole compound is environmentally friendly, convenient to operate, safe, cheap and efficient. Compared with the prior art, the method is applied to a large quantity of functional groups, high in yield, simple to operate, safe, low in cost and environmentally friendly and produces a few byproducts.

Aerobic visible-light photoredox radical C-H functionalization: Catalytic synthesis of 2-substituted benzothiazoles

An aerobic visible-light driven photoredox catalytic formation of 2-substituted benzothiazoles through radical cyclization of thioanilides has been accomplished. The reaction features C-H functionalization and C-S bond formation with no direct metal involvement except the sensitizer. The reaction highlights the following: (1) visible-light is the reaction driving force; (2) molecular oxygen is the terminal oxidant, and (3) water is the only byproduct.

Palladium-catalyzed synthesis of 2-substituted benzothiazoles via a C-H functionalization/intramolecular C-S bond formation process

(Chemical Equation Presented) Catalytic synthesis of 2-substituted benzothiazoles from thiobenzanilides was achieved in the presence of a palladium catalyst through C-H functionalization/C-S bond formation. This method features the use of a novel catalytic system consisting of 10 mol % of Pd(II), 50 mol % of Cu(I), and 2 equiv of Bu4NBr that produced variously substituted benzothiazoles in high yields with good functional group tolerance.

Conversion of thiobenzamides to benzothiazoles via intramolecular cyclization of the aryl radical cation

A new and general method has been developed for the intramolecular cyclization of thiobenzamides to benzothiazoles via aryl radical cations as reactive intermediates. The method utilizes phenyliodine(III) bis(trifluoroacetate) (PIFA) in trifluoroethanol or cerium ammonium nitrate (CAN) in aqueous acetonitrile at room temperature to effect cyclization within 30 min in moderate yields.

Synthesis of benzothiazoles via ipso substitution of ortho- methoxythiobenzamides

An efficient route to the synthesis of benzothiazoles from orthoo-methoxythiobenzamides via the ipso substitution of an aromatic methoxy group is presented, and the mechanism of the Jacobson synthesis of benzothiazoles is further investigated.

Novel series of O-substituted 8-quinolines and 4-benzothiazoles as potent antagonists of the bradykinin B2 receptors

The synthesis and the SAR study of novel O-substituted 8-quinolines and 4-benzothiazoles as highly potent non-peptide bradykinin B2 receptor antagonists are described. Several members of this series of antagonists efficiently inhibited the BK-induced vasoconstriction on different isolated organ preparations.

Structural Studies on Bioactive Compounds. 23. Synthesis of Polyhydroxylated 2-Phenylbenzothiazoles and a Comparison of Their Cytotoxicities and Pharmacological Properties with Genistein and Quercetin

A series of polyhydroxylated 2-phenylbenzothiazoles 3 has been prepared by demethylation of the precursor methoxylated 2-phenylbenzothiazoles 9.The key step in the construction of the benzothiazole nucleus involves a Jacobson cyclization of methoxylated thiobenzanilides 8.The target compounds inhibit WiDr human colon tumor cells and MCF-7 human mammary tumor cells in vitro with IC50 values in the low micromolar range, but the activity against MCF-7 cells is not related to estrogen receptor-binding affinity.None of the compounds showed selective cytotoxicity againstAbelson virus-transformed ANN-1 cells encoded with the pp120gag-abl tyrosine kinase compared with the parental 3T3 line.Compounds were only marginally inhibitory to the EGF receptor-associated protein tyrosine kinase from a membrane preparation of A431 cells.The most active compound was 4,6-dihydroxy-2-(4-hydroxyphenyl)benzothiazole (3b) which has the same overall hydroxyl substitution pattern as genistein (1a).The compounds were weakly cytotoxic for an EGF receptor, overexpressing cell line HN5, but when tested for differential toxicity against the EGF receptor tyrosine kinase or the PDGF receptor tyrosine kinase in a standard mitogenesis assay utilizing human fibroplasts, no discrimination was observed.In this assay, the compounds inhibited DNA synthesis when added to cells during S phase.This suggests that inhibition could not be interpreted in terms of tyrosine kinase inactivation but more likely as a relatively broad specificity for the ATP-binding domain of other kinases such as thymidine kinase.