188483-20-7

Upstream product

• 955-83-9 2,5-diphenylfuran 
• 1445-78-9 2,5-Diphenyl-thiophene 
• 851-33-2 1,2,5-triphenyl-1H-pyrrole 
• 855-31-2 1-(4-methoxyphenyl)-2,5-diphenyl-1H-pyrrole 
• 191402-10-5 triphenyl-λ⁶-sulfanenitrile 
• 802-22-2 (2,5-diphenyl-pyrrol-1-yl)-carbamic acid tert-butyl ester 
• 857-30-7 1-(4-nitrophenyl)-2,5-diphenyl-1H-pyrrole 
• 94905-31-4 2,5-diphenyl-pyrrole-1-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Reaction of furans with trithiazyl trichloride: New synthesis of isothiazoles

Trithiazyl trichloride 1 converts 2,5-disubstituted furans into isothiazoles (e.g. 3, 6, 7) regiospecifically and in good yield, providing a new, one-step synthesis of isothiazoles, for which a novel mechanism involving formation and ring-opening of a β-t

The ready conversion of 2,5-disubstituted furans into isothiazoles

Various 2,5-disubstituted furans are very readily and efficiently transformed into 5-acyl-3-substituted isothiazoles by the action of ethyl carbamate, thionyl chloride and pyridine.

Generation of sulfenylnitrenes by N-sulfenylation of triphenyl-λ6-sulfanenitrile

The sulfenylation of triphenyl-λ6-sulfanenitrile (1) with 2,4-dinitrobenzenesulfenyl chloride in the presence of alkenes affords aziridines together with triphenylsulfonium salt. The reaction of 1 with sulfur dichloride also generates ClSN whic

One-step synthesis of 5-acylisothiazoles from furans

Premixed ethyl carbamate, thionyl chloride and pyridine (which generate thiazyl chloride, N≡SCl) in boiling benzene or toluene convert 2,5- and 2,3,5-substituted furans into 5-acylisothiazoles regiospecifically. The reactions are much faster and generally higher yielding in boiling chlorobenzene with more thionyl chloride and with pyridine or isoquinoline as base. Under the more vigorous conditions, even fully substituted 3-bromofurans give isothiazoles, with the displacement of bromine. Deactivated furans, with electron-withdrawing groups such as ester, cyano, benzoyl and phenylsulfonyl in the α-position, react under the more vigorous conditions to give 5-acylisothiazoles with the electronegative group in the 3-position. The 'activated' 2-methyl-5-phenyl- and 5-phenyl-2-phenylthio-furans react analogously, with the more electron-releasing group becoming part of the 5-acyl substituent, exclusively or predominantly. These results are explained by initial electrophilic attack of the furan ring to give a β-thiazyl derivative which spontaneously ring-opens and closes to the isothiazole. The X-ray structures of five of the differently substituted isothiazole compounds are reported. All have very similar patterns of bonding within their isothiazole rings that appear to be independent of the electron-withdrawing or -donating nature of the substituents. Three of the compounds (8a, 8g and 13) have loosely linked chain structures in the solid state, adjacent molecules being connected by combinations of hydrogen bonding and π-π stacking interactions.

Conversion of pyrroles into bi-1,2,5-thiadiazoles: A new route to biheterocycles

Trithiazyl trichloride 1 converts 1,2,5-triphenylpyrrole 5 into its 3,4-dichloro derivative together with the isothiazole imine 6 and the imine hydrolysis product, the ketone 3. The best yield of the isothiazole 6 is obtained in the presence of 4 A molecular sieves (Table 1). Conversion of the pyrrole 5 into the isothiazole 6 is exactly analogous to the reaction of 1 with 2,5-diphenyl-furan and -thiophene. Other N-aryl and the related 2,5-diphenylpyrroles 8 give similar results (Table 2). However, 1-methyl-2,5-diphenylpyrrole 11 reacts with 1 in an entirely different way to give 4,4′-diphenyl-3,3′-bi-1,2,5-thiadiazole 12, in which two thiadiazole rings have been fused onto the pyrrole and the CH3N unit has been excised as HCN. The same product 12 is formed, in similar yields, by reaction of 1 with 1,4-diphenylbuta-1, 3-diyne and 1,4-diphenylbut-1-en-3-yne. Other N-alkyl 2,5-diphenylpyrroles 16 react similarly (Table 3), giving the best yield (70%) of bi-thiadiazole 12 in the presence of 4 A molecular sieves (Table 4). 1-Methyl- and 1-ethyl-3,4-dibromo-2,5-diphenylpyrrole also give 12, together with 3-(benzoyldichloromethyl)-4-phenyl-1,2,5-thiadiazole 21 in high combined yield. The formation of bi-1,2,5-thiadiazole 12 from N-alkylpyrroles represents a new dissection of the pyrrole ring and a new and very short route to an aromatic biheterocyclic system. Mechanisms which rationalise the different pathways observed are proposed for all of these reactions.

Reaction of furans with trithiazyl trichloride: A new synthesis of isothiazoles

Trithiazyl trichloride 1 converts 2,5-diphenylfuran into 5-benzoyl-3-phenylisothiazole 2 regiospecifically and in high yield. This is a new ring opening of furans and a new synthesis of isothiazoles. 2,5-Bis(4-methylphenyl)furan, 3-bromo-2,5-diphenylfuran, 2,3,5-triphenylfuran, 2,5-di-tert-butylfuran and its 3-chloro and 3-bromo derivatives react in an entirely analogous manner to give the corresponding isothiazoles (55-85%) in synthetically useful, one-pot, conversions. 2,5-Diphenylthiophene reacts more slowly with the trimer 1 to give the same product, 2, as the corresponding furan, probably by oxidation of the analogous thiobenzoyl compound by the reagent, which is shown to oxidise thiobenzophenone to benzophenone very rapidly. Tetraphenylcyclopentadienone 8 reacts rapidly with the trimer to give 3,4,5,6-tetraphenyl-2(1H)-pyridone 10 (56%). Possible mechanisms in which the monomer, Cl-S≡N, is the reacting species are proposed for all of these reactions.