22388-07-4

Upstream product

• 42477-57-6 3-allylbenzothiazoline-2-thione 
• 106-95-6 allyl bromide 
• 2492-26-4 sodium 2-mercaptobenzothiazole 
• 7778-70-3 potassium 2-mercaptobenzothiazolate 
• 149-30-4 2-Mercaptobenzothiazole 
• 107-05-1 3-chloroprop-1-ene 
• 65605-48-3 benzothiazol-2-thione, triethylammonium salt 
• 64370-08-7 p-nitrobenzyl (2R,3R)-2-(benzothiazol-2'-yldithio)-α-isopropylidene-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 35466-83-2 allyl methyl carbonate 
• 556-56-9 allyl iodid 
• 107-18-6 allyl alcohol 
• 3116-52-7 N,N'-diisopropyl-O-allylisourea 
• 54420-88-1 S-(benzothiazol-2-yl) allyl thiocarbonate 

Downstream Products

• 42477-57-6 3-allylbenzothiazoline-2-thione 
• 95-16-9 1,3-Benzothiazole 
• 2179-57-9 diallyl disulphide 
• 592-88-1 diallyl sulphide 
• 4271-09-4 2,2'-benzothiazolyl 

Relevant academic research and scientific papers

Synthesis, characterization, and antitumor activity of some novel S-functionalized benzo[d]thiazole-2-Thiol derivatives; Regioselective coupling to the-SH group

Several 2-substituted sulfanyl benzo[d]thiazoles were regioselectively synthesized by the reaction of benzo[d]thiazole-2-Thiol (1a) with a variety of reagents under different basic conditions. Some 2-(2,3-disubstituted propyl sulfanyl)benzo[d]thiazoles were obtained from 2-(allylthio)benzo[d]thiazole, which was prepared by the allylation of 1a with allyl bromide in the presence of sodium hydride in dry N,N-dimethylformamide. Reaction of 1a with various pyrazolyl-quinoxaline derivatives was also investigated. Better yields and shorter reaction time were achieved for the synthesis of some derivatives by using ultrasound irradiation. The structural elucidation of all compounds was based on both analytical and spectroscopic data. The newly synthesized compounds were tested in vitro for their antitumor activity against Ehrlich ascites carcinoma (EAC) cells grown in albino mice. Doxorubicin was used as a standard antitumor antibiotic, and some compounds showed half maximal inhibitory concentration (IC50) in the range 40-68 μg mL-1.

Synthesis, characterization, and preliminary in vitro cytotoxic evaluation of a series of 2-substituted benzo [d] [1,3] azoles

A series of benzo [d] [1,3] azoles 2-substituted with benzyl-and allyl-sulfanyl groups were synthesized, and their cytotoxic activities were in vitro evaluated against a panel of six human cancer cell lines. The results showed that compounds BTA-1 and BMZ

Unexpected cis-selectivity in (Sylvestre) Julia Olefinations with Bu 3Sn-containing allyl benzothiazolyl sulfones: Stereoselective synthesis of 1,3-butadienyl- and 1,3,5-hexatrienylstannanes

Bu3Sn-substituted benzothiazolyl sulfones 1c, 1d, and 1f were subjected to Julia olefmation reactions with a variety of aldehydes. cis-Selectivities up to 97:3 were obtained by using KHMDS as base in THF.

A New Approach to the Synthesis of Benzothiazole, Benzoxazole, and Pyridine Nucleosides as Potential Antitumor Agents

A modified nitrogen and sulfur glycosylation reaction involving benzothiazole benzoxazole and pyridine nucleoside bases with furanose and pyranose sugars are described. Conformational analysis has been studied by homo- and heteronuclear two-dimensional NMR methods (2D DFQ-COSY, HMQC and HMBC). The N and S sites of glycosylation were determined from the 1H, 13C heteronuclear multiple-quantum coherence (HMQC) experiments. All the deprotected nucleosides were tested for their potential antitumor activity.

Ligand Rearrangement Leads to Tetrahydrothiophene-Functionalized N,S-Heterocyclic Carbene Palladium(II) Complexes

Tetrahydrothiophene-functionalized N,S-heterocyclic carbene palladium(II) complexes are synthesized through an unexpected rearrangement that proceeds with palladium(II) trifluoroacetate but not with palladium(II) acetate, palladium(II) bromide, or palladium(II) chloride. A series of these complexes were isolated and characterized by X-ray crystallography. The mechanism of formation of these [3.2.1]palladabicycles was explored, and the catalytic capabilities of these complexes were demonstrated in representative C-C coupling reactions.

Selective and mild sulfoxidation of 2-sulfylbenzothiazole using hydroperoxides derived from cyclohexanone in the absence of catalyst

Alkyl hydroperoxides derived from cyclohexanone are attractive oxidants because they are easily available, more reactive than TBHP but much less acidic than m-CPBA. Wherein 1,1′-peroxybis(1-hydroperoxycyclohexane) (C) can be generated by the current simply method and displays the excellent reactivity and selectivity based on oxidative reactions of various benzothiazolyl sulfides substituted by different function groups. The research found that the reactions can be performed in the absence of catalyst and under very mild conditions optimized. Yields of sulfoxides is higher than 90%, no or a little reaction happened at the proximal double bond、 N and S atoms in the benzothiazolyl moiety. Phenyl sulfide as the substrates was also examined for the reaction scope test. The results show that they were uniquely and completely oxidized to sulfoxides in 1 h. A mild, environmentally friendly, catalyst-free aryl sulfide sulfoxidation method has been developed.

Isomerisation of Vinyl Sulfones for the Stereoselective Synthesis of Vinyl Azides

Reported is the construction, and facile base-mediated conversation of ten differently substituted 3-azido E-vinyl sulfones (γ-azido-α,β-unsaturated sulfones) into their isomeric vinyl azide counterparts. The requisite 3-azido E-vinyl sulfones were prepared from 3-bromo E-vinyl sulfones, which in turn were accessed from allyl sulfones via a bromination-elimination sequence. In relation to this a one-pot azidation-isomerisation sequence was developed which enabled the direct formation of the vinyl azides from the corresponding 3-bromo E-vinyl sulfones. Similarly, a convenient one-pot Horner–Wadsworth–Emmons olefination-isomerisation approach was utilised in order to prepare some of the allylic sulfones used in this study. The vinyl azide forming process typically proceeded with high levels of Z-selectivity, although this was dependent on the vinyl sulfone substitution pattern. Thus, with either no substituent or a methyl group in the γ- or β-position, relative to the sulfone, good, to high levels of Z-selectivity (Z/E = 85:15 to ≥ 95:5) were obtained. However, incorporation of an α-sulfonyl methyl substituent led to an E-selective process (Z/E = 20:80). A non-bonding interaction between the azido group and the α-sulfonyl vinylic proton is proposed, which acts as a conformational control mechanism to help guide the stereochemical outcome.

Three-Component Synthesis of 2-Substituted Thiobenzoazoles Using Tetramethyl Thiuram Monosulfide (TMTM) as Thiocarbonyl Surrogate

A metal-free synthesis of 2-benzyl/allyl-substituted thiobenzoazoles was developed starting from tetramethyl thiuram monosulfide (TMTM) which served as thiocarbonyl surrogate. By using 2-aminophenols (or 2-aminothiophenols, or 1,2-phenylenediamines) and TMTM as starting materials, 2-mercaptobenzoazoles could be synthesized efficiently. The subsequent C–S bond formation with benzyl/allyl halides gave the final products (2-benzyl/allyl-substituted thiobenzoazoles) with good to excellent yields. The metal-free conditions, inexpensive and easily available starting materials, and broad substrate scope are the advantageous features of this protocol.

One-Pot Synthesis of 2-Benzyl/2-Allyl-Substituted Thiobenzoazoles Using Transition-Metal-Free Conditions in Water

A transition-metal-free protocol for the one-pot synthesis of 2-benzyl/2-allyl-substituted thiobenzoazoles in water was developed. The cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) gave mercapto benzoheterocycles, and the subsequent C-S coupling with benzyl or allyl halides furnished the desired products in good to excellent yields. This method features transition-metal-free conditions with water as a solvent, an easy performance, mild reaction conditions, a wide substrate scope, and good to excellent yields, thus paving an efficient and useful way to establish a library of potentially active drug molecules.

Ruthenium-catalyzed decarboxylative C-S cross-coupling of carbonothioate: synthesis of allyl(aryl)sulfide

A novel ruthenium-catalyzed decarboxylative cross-coupling of carbonothioate is disclosed. This method provides straightforward access to the corresponding allyl(aryl)sulfide derivatives in generally good to excellent yields under mild conditions and feat