215436-24-1

Basic information

• Product Name: 5-(TOSYLOXYIMINO)-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE
• Synonyms: 5-(TOSYLOXYIMINO)-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE
• CAS NO: 215436-24-1
• Molecular Formula: C₁₃H₁₃NO₇S
• Molecular Weight: 327.31
• Mol File: 215436-24-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 155-156 °C
• Boiling Point: 417.4±38.0 °C(Predicted)
• Appearance: /
• Density: 1.44±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 5-(TOSYLOXYIMINO)-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(TOSYLOXYIMINO)-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE(215436-24-1)
• EPA Substance Registry System: 5-(TOSYLOXYIMINO)-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE(215436-24-1)

Safety Data

• Hazardous Substances Data: 215436-24-1(Hazardous Substances Data)

Upstream product

• 2033-24-1 cycl-isopropylidene malonate 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1071068-55-7 Toluene-4-sulfonic acid 5,9,9-trimethyl-7,11-dioxo-8,10-dioxa-1-aza-spiro[5.5]undec-3-en-1-yl ester 
• 1071111-50-6 Toluene-4-sulfonic acid 3-tert-butyl-9,9-dimethyl-7,11-dioxo-8,10-dioxa-1-aza-spiro[5.5]undec-3-en-1-yl ester 
• 1027940-16-4 Toluene-4-sulfonic acid 3-butyl-9,9-dimethyl-7,11-dioxo-8,10-dioxa-1-aza-spiro[5.5]undec-3-en-1-yl ester 
• 1071092-63-1 Toluene-4-sulfonic acid 3,5,9,9-tetramethyl-7,11-dioxo-8,10-dioxa-1-aza-spiro[5.5]undec-3-en-1-yl ester 
• 768368-54-3 Toluene-4-sulfonic acid 3,9,9-trimethyl-7,11-dioxo-8,10-dioxa-1-aza-spiro[5.5]undec-3-en-1-yl ester 
• 6784-22-1 phenylcarbamoyl cyanide 
• 615-16-7 1,3-dihydro-2H-benzimidazol-2-one 
• 59-49-4 2-Benzoxazolinone 
• 3459-92-5 DBC 
• 1027146-44-6 Toluene-4-sulfonic acid 9,9-dimethyl-7,11-dioxo-3-((S)-3-triisopropylsilanyloxy-butyl)-8,10-dioxa-1-aza-spiro[5.5]undec-3-en-1-yl ester 

Relevant articles and documents

Preparation of substituted pyridines via regiocontrolled [4 + 2] cycloadditions of oximinosulfonates: Methyl 5-methylpyridine-2-carboxylate [(2-pyridinecarboxylic acid, 5-methyl-, methyl ester)]

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Synthesis of substituted pyridines via regiocontrolled [4 + 2] cycloadditions of oximinosulfonates

Diels-Alder cycloadditions of oximinosulfonate 8 with a variety of 1, 3-dienes proceed with regiochemistry opposite to that observed with conventional imino dienophiles, providing expeditious synthetic routes to substituted pyridines, tetrahydropyridines, and pyrrolines. The oximinosulfonate 8 is prepared in one convenient synthetic operation from Meldrum's acid and reacts with conjugated dienes at -78 C in the presence of 2 equiv of dimethylaluminum chloride to afford [4 + 2] cycloadducts in good to excellent yield. Exposure of these cycloadducts to the action of NaOMe and JV-chlorosuccinimide in methanol-THF at room temperature then produces substituted pyridines. The utility of this new two-step annulation protocol is demonstrated in total syntheses of the pyridine alkaloids fusaric acid and (S)-(+)-fusarinolic acid. Heating the [4 + 2] cycloadducts derived from 8 in a mixture of acetonitrile and pH 7 phosphate buffer induces an unusual Stieglitztype rearrangement leading to the formation of interesting spirobicyclic pyrrolines.