215436-24-1

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 
• 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 
• 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 

Relevant academic research and scientific papers

Cyanocarbonylation of amines with 5-tosyloxyimino-2,2-dimethyl-1,3- dioxane-4,6-dione

5-Tosyloxyimino-2,2-dimethyl-1,3-dioxane-4,6dione (3), prepared by the reaction of 5-hydroxyimino-2,2dimethyl-1,3-dioxane-4,6-dione sodium salt (2) with tosyl chloride, was treated with various amines (4a-c and 6a,b) in the presence of triethylamine to give the corresponding N-cyanocarbonyl derivatives (5a-c and 7a,b). However, reaction of 3 with benzyl alcohol gave rise to the formation of dibenzyl carbonate (10).

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.