1004-37-1

Usage

Uses

Used in Organic Synthesis:
2,6-DIMETHYLPYRAN-4(4H)-THIONE is used as a reagent in organic synthesis for the preparation of various sulfur-containing compounds. Its unique structure allows it to be a valuable building block in the creation of complex organic molecules.
Used in Pharmaceutical Research:
Due to its potential biological activities, including antimicrobial and antioxidant properties, 2,6-DIMETHYLPYRAN-4(4H)-THIONE is used in pharmaceutical research as a starting material for the development of new drugs and therapeutic agents.
Used in Chemical Research:
2,6-DIMETHYLPYRAN-4(4H)-THIONE is of interest to researchers and chemists for its structural and functional properties, making it a subject of study for various scientific applications, including the exploration of new chemical reactions and the synthesis of novel compounds.
Used in Industrial Applications:
Although specific applications are limited, 2,6-DIMETHYLPYRAN-4(4H)-THIONE's unique properties may find use in various industrial processes, particularly in the development of new materials and chemical intermediates.

InChI:InChI=1/C7H8OS/c1-5-3-7(9)4-6(2)8-5/h3-4H,1-2H3

Upstream product

• 1004-36-0 2,6-dimethylpyrone 
• 19172-47-5 Lawessons reagent 
• 114538-26-0 2,6-dimethyl-4-methylseleno-pyrylium; iodide 
• 7732-18-5 water 
• 10207-41-7 2,6-dimethyl-4H-pyran-4-selenone 
• 71-43-2 benzene 
• 40815-98-3 Epidithio-(2,4)-heptadienon-(6) 

Downstream Products

• 6276-13-7 4-allylmercapto-2,6-dimethyl-pyrylium; iodide 
• 6276-18-2 2,6-dimethyl-4-(4-nitro-benzylsulfanyl)-pyrylium; iodide 
• 5397-57-9 2,6-dimethyl-4-(2-oxo-2-[2]phenanthryl-ethylsulfanyl)-pyrylium; bromide 
• 6276-19-3 4-benzylsulfanyl-2,6-dimethyl-pyrylium; 4-bromo-benzenesulfonate 
• 28286-88-6 4-dicyanomethylene-2,6-dimethyl-4H-pyran 
• 100623-08-3 2-(2-chloro-trans-styryl)-6-methyl-pyran-4-thione 
• 100621-85-0 3-benzoyl-2,6-dimethyl-pyran-4-thione 
• 6275-20-3 2,6-dimethyl-4-(4-phenyl-phenacylmercapto)-pyrylium; bromide 
• 74332-95-9 4-benzylsulfanyl-2,6-dimethyl-pyrylium; iodide 
• 13895-74-4 ethyl 2-cyano-2-(2,6-dimethyl-4H-pyran-4-ylidene)acetate 
• 5330-72-3 2,6-dimethyl-4-phenacylmercapto-pyrylium; bromide 
• 5330-68-7 2,6-dimethyl-4-(4-methyl-phenacylmercapto)-pyrylium; bromide 
• 5335-41-1 4-(p-bromophenacyl)mercapto-2,6-dimethylpyrylium bromide 
• 7621-99-0 4-ethoxycarbonylmethylsulfanyl-2,6-dimethyl-pyrylium; iodide 

Relevant academic research and scientific papers

A practical synthesis of an anti-methicillin resistant Staphylococcus aureus cephalosporin BMS-247243

A practical synthesis of the anti-methicillin resistant Staphylococcus aureus cephem (6R-trans)-E-7-[[[[2,5-dichloro-4-[3-[(carboxymethyl)amino]-3-oxo-1-propenyl] phenyl]-thio]-acetyl]amino]-4-[[(2-carboxy-8-oxo-5-thia-1-azabicyclo-[4.2.0]oct- 2-en-3-yl)methyl]thio]-2,6-dimethyl-1-[3-(4-methylmorpholino-4-yl)propyl]-1- pyridinium, hydroxide, inner salt (BMS-247243) was developed. A process was developed for the interchange of the iodide counterion in 3a to chloride 3b that was essential for an efficient synthesis of the C-3 side chain 4-mercaptopyridone 6b. Use of catalytic Bu4NCl in the reaction of chlorocinnamide 14 with the Li-salt of methylthioglycolate formed the methyl ester of the C-7 side chain 12b in high yield. Reaction with the dianion of thioglycolic acid gave an increased level of the corresponding Michael addition byproduct that led to lower quality thermodynamic product 12b by the reverse reaction. Cephem nucleus 16 was acylated with the acid chloride of acid 12b in a biphasic system to circumvent the cumbersome workup involved in reactions mediated by carbodiimdes DCC or EDAC for the synthesis of diester 17. An unusual degradation product diacid 20 was obtained during the deprotection of diester 17 with TFA to amorphous diacid 19. Reaction of diacid 19 with 4-mercaptopyridone 6b formed BMS-247243 in moderate yield. Alternately, an efficient coupling of diester 17 with 4-mercaptopyridone 6b gave crystalline diester 21 with minimal (1%) contamination of the double bond isomer 22. Double deprotection of diester 21 followed by crystallization furnished the double zwitterion BMS-247243 in high yield.

ORGANOPHOSPHORUS CHEMISTRY, 20. THE BEHAVIOUR OF CERTAIN γ-PYRONE DERIVATIVES TOWARD 2,4-BIS-(4-METHOXYPHENYL)-1,3,2,4-DITHIAPHOSPHETAN-2,4-DISULPHIDE (LAWESSON REAGENT)

Lawesson reagent LR, 1 converts 2,6-dimethyl-γ-pyrone 2a, flavone 3a into their corresponding thioketones 2b and 3b in high yields.Thiation of flavone 3a with Lawesson reagent LR, 1 can be also induced photochemically to give thioflavone 3b together with the ring phosphorane product 6A.Thiation of khellin 4a by LR to give 4b is accompanied by demethylation of 4b to give desmethylthiokhellin 4c.The behaviour of γ-pyrones 2a, 3a and 4a toward thiation with LR, 1 was discussed in the light of the principle of vinylogy.

Pyran Annelation: An Effective Route to a Tricyclic Dienone

A new pyran annelation reaction was investigated. 2,6-Dimethyl-4H-pyran-4-one (2) was converted to 2((p-tolylsulfonyl)methyl)-6-methyl-4H-pyran-4-one (7) which was alkylated at the C-2 methylene position regioselectively, and the p-tolylsulfonyl group can be easily eliminated with an aluminium amalgam reduction.On the other hand the pyran-4-one ring was easily transformed into an 1,5-diketone derivative.By joining and applying these selective alkylations and transformations, tricyclic dienone 22 was effectively synthesized from 2.

SYNTHESES OF VINYLOGOUS 4H-PYRONES FROM 2,6-DIMETHYL-4H-PYRAN-4-THIONE AND ARENYL BROMOMETHYL KETONES

2,6-Dimethyl-4H-pyran-4-ylideneacetophenones (5) were prepared by desulfurization of mercaptopyrilium salts (4) with diazabicycloundecene (DBU) in moderate yield.The 1H NMR spectra in CDCl3 solution of 5 show the exclusive preference for s-cis conf