62686-84-4

Usage

InChI:InChI=1/C9H13NO2/c1-6(11)9(7(2)12)8-4-3-5-10-8/h10H,3-5H2,1-2H3

Upstream product

• 5264-35-7 2-methoxy-1-pyrroline 
• 123-54-6 acetylacetone 

Downstream Products

• 1357027-01-0 3-methyl-4-(4-methylphenyldiazenyl)-1,1-diphenyl-6,7-dihydro-5H-pyrrolo[1,2-c][1,3,2λ4]oxazaborine 
• 1357027-13-4 4-acetyl-2-(4-methylphenyl)-1,1-diphenyl-2,5,6,7-tetrahydro-1H-pyrrolo[1,2-d][1,2,4,3λ4]triazaborine 

Relevant academic research and scientific papers

Synthesis of [1,2-A]-fused tricyclic dihydroquinolines by palladiumcatalyzed intramolecular C-N cross-coupling of polarized heterocyclic enamines

A simple methodology for [1,2-A]-fused tricyclic dihydroquinolines is established. The key ste of the methodology is an intramolecular Buchwald-Hartwig amination reaction of suitabl halogenated (both bromo and chloro) cyclic enaminoketones, enaminoesters and enaminonitrile with various ring size (from five-to seven-membered). Optimal reaction conditions (palladiu source, base, ligand) depend on the ring size of the starting enamine, giving 65-98% yield of th tricyclic product. A treatment of the products with perchloric acid gives respective quinoliniu perchlorates.

A new bicyclic oxazaborines with a bridged nitrogen atom, their thermic rearrangement and fluorescence properties

Cyclic β-enaminones bearing secondary amino group react with 4-substituted benzenediazonium tetraphenylborates in dichloromethane to form substituted bicyclic [1,3,2λ4]oxazaborines The oxazaborines rearrange, on heating to 200 °C in the absence of solvent or in DMF or DMSO, to isomeric 2H-[1,2,4,3λ4]triazaborines. Previously prepared [1,3,2λ4]oxazaborines derived from acyclic β-enaminones bearing secondary amino group either did not undergo the rearrangement or with a lot of difficulties and with negligible yield. The fluorescence behaviour of the prepared triazaborines was observed. These compounds fluoresce in 2-methyltetrahydrofurane and in solid state under low temperatures.

Synthesis of acetyl-substituted heterocyclic enamines and their reaction with diethyl azodicarboxylate

Acetyl-substituted heterocyclic enamines 4 were synthesized from lactim ethers 2 and acetylacetone through condensation and deacetylation reactions, and they, along with the ester-substituted heterocyclic enamines 6, reacted with diethyl azodicarboxylate to afford C-adducts 7 and 8 in excellent yields.