Synthesis of fluorophenothiazines via Smiles rearrangement and their conversion into sulfones

Sharma, Neerja; Kumar, M.; Gupta, R.

doi:10.1016/s0022-1139(99)00098-6

Cited by 30 publications

(9 citation statements)

References 8 publications

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“…(B) 2-Aminobenzothiazoles and 2-aminobenzenethiols can be conveniently prepared from aryl amines substituted or unsubstituted at para positions. [41][42][43][44][45][46][47][48][49][50][51][52] This method involves two steps: In the first step, hydrochloride of substituted arylamine is treated with KCNS or NH 4 SCN to obtain corresponding phenylthiourea. The second step involves brominative cyclization of phenylthiourea by bromine and chloroform to provide the corresponding 2-aminobenzothiazole.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Starting Heterocycles: 2-Aminobenzothiazoles, 2-Aminothiazoles and 2-Aminobenzenethiols – Potential Precursors for Macroheterocycles

Sharma¹

2018

MHC

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Section: Methodsmentioning

confidence: 99%

Synthesis of Starting Heterocycles: 2-Aminobenzothiazoles, 2-Aminothiazoles and 2-Aminobenzenethiols – Potential Precursors for Macroheterocycles

Sharma¹

2018

MHC

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“…2-Iodo-4,5-dimethylaniline and 4,5-dichloro-2-iodoaniline were converted into 2-amino-4,5dimethylbenzenethiol and 2-amino-4,5-dichlorobenzenethiol as per the procedures reported in the literature. 27,28 In our attempts to synthesise Schiff base ligands using aldehyde and amines, the prepared new ligands, i.e. (E)-3-(((2mercaptophenyl)imino)methyl)pyridine-2-thiol (MPPT), (E)-3-(((2-mercapto-4,5-dimethylphenyl)imino)methyl)pyridine-2-thiol (DMPMPT) and (E)-3-(((4,5-dichloro-2-mercaptophenyl)imino)methyl)pyridine-2-thiol (DCMPPT), containing two thiols and one imine group were characterized by mass, SEM, IR, Raman, UV and NMR spectral investigations.…”

Section: Methodsmentioning

confidence: 99%

New photocatalyst for allylic aliphatic C–H bond activation and degradation of organic pollutants: Schiff base Ti(iv) complexes

et al. 2015

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The Schiff's base metal complexes have been concerned significantly due to their out-of-box applications in the environmental quantum leap by mineralization of the organic pollutants to fewer harmful byproducts and oxygen generation such as photosynthesis process. The Ti 4+ complexes obtained from Schiff base ligands reacted with donor atoms such as S and N under solvothermal conditions. These complexes were characterized using the microanalysis, conductivity studies, and different spectral techniques. From these data reveals that the compound shows distorted octahedral geometry with ligands coordination via azomethine nitrogen and thiol sulfur atoms. Oxidation of allylic methyl group examined the photocatalytic activity of [Ti(L)O] under ambient conditions and oxidative and cyclization under visible light irradiation. Ti(DCMPPT)O complex is very efficient catalyst due to the very short span of time convert aldehydes from allylic compounds. Aldehydes ready to react with 2-aminophenol or 2-aminobenzenethiol to produce (E)-2-styrylbenzo[d]oxazoles and (E)-2-styrylbenzo[d]thiazoles. Due to the suitable of the bandgap energy of nature to the generation of • OH radicals during the catalytic reaction. For this reason, higher oxidation rate. [Ti(DCMPPT)O] as a very efficient photocatalyst for degradation of MB, due large surface area and that supports to lower recombination energy mechanism.

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“…Numerous different synthesis strategies of phenothiazines were drawn up in the past decades, including heat treatment of diphenylamines and sulfur at high temperature or a four-step route via Smiles rearrangement . Despite indisputable advances, the heterocyclization step continues to be insufficient.…”

Section: Introductionmentioning

confidence: 99%

Copper-Loaded Layered Bismuth Subcarbonate—Efficient Multifunctional Heterogeneous Catalyst for Concerted C–S/C–N Heterocyclization

Kocsis

Ötvös

Samu

et al. 2021

ACS Appl. Mater. Interfaces

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An efficient self-supported Cu(II)Bi(III) bimetallic catalyst with a layered structure was designed and developed. By careful characterization of the as-prepared material, the host structure was identified to exhibit a Sillen-type bismutite framework, with copper(II) ions being loaded as guests. The heterogeneous catalyst enabled C–N and C–S arylations under mild reaction conditions and with high chemoselectivities, thus furnishing valuable phenothiazines via heterocyclization with wide substrate tolerance. As corroborated by detailed catalytic studies, the cooperative, bifunctional catalyst, bearing Lewis acid sites along with copper(II) catalytic sites, facilitated an intriguing concerted C–N/C–S heterocyclization mechanism. The heterogeneous nature of the catalytic reactions was verified experimentally. Importantly, the catalyst was successfully recycled and reused multiple times, persevering its original structural order as well as its initial activity.

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Synthesis of fluorophenothiazines via Smiles rearrangement and their conversion into sulfones

Cited by 30 publications

References 8 publications

Synthesis of Starting Heterocycles: 2-Aminobenzothiazoles, 2-Aminothiazoles and 2-Aminobenzenethiols – Potential Precursors for Macroheterocycles

Synthesis of Starting Heterocycles: 2-Aminobenzothiazoles, 2-Aminothiazoles and 2-Aminobenzenethiols – Potential Precursors for Macroheterocycles

New photocatalyst for allylic aliphatic C–H bond activation and degradation of organic pollutants: Schiff base Ti(iv) complexes

Copper-Loaded Layered Bismuth Subcarbonate—Efficient Multifunctional Heterogeneous Catalyst for Concerted C–S/C–N Heterocyclization

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