127943-91-3

Upstream product

• 75-52-5 nitromethane 
• 106-49-0 p-toluidine 
• 123187-51-9 2-acetyl-5-oxo-pentanoic acid methyl ester 
• 105-45-3 acetoacetic acid methyl ester 
• 1266617-35-9 methyl 2-butoxy-6-methyl-3,4-dihydro-2H-pyran-5-carboxylate 
• 99789-32-9 2-Ethoxy-3,4-dihydro-6-methyl-2H-pyran-5-carbonsaeure-methylester 
• 930-68-7 cyclohexenone 
• 17640-15-2 methyl cyanoformate 

Downstream Products

• 1048671-23-3 C₁₇H₂₀O₆ 
• 1048671-22-2 C₁₅H₁₆O₄ 
• 1048671-21-1 C₁₄H₁₄O₃ 
• 1048671-25-5 C₂₁H₂₃NO₅ 
• 1048671-26-6 C₂₂H₂₅NO₆ 
• 1048671-24-4 C₁₇H₂₀O₆ 

Relevant academic research and scientific papers

Synthesis of tetrahydropyridine derivatives through a modular assembly reaction using 3,4-dihydropyran as dual substrate and template

A concise method to synthesize 1,2,3,4-tetrahydropyridines is described that involves the use of 2-alkoxy-3,4-dihydropyran as a modular precursor to react with aniline and a nucleophile. In this method, the heteroatom of the dihydropyran ring was replaced by nitrogen of aniline while the nucleophile attached to its adjacent position. Various druglike polyheterocycles were prepared with this method by using NH2-containing 1,5- or 1,4-bisnucleophiles.

REGIOSELECTIVE SYNTHESIS OF β-KETOESTERS FROM LITHIUM ENOLATES AND METHYL CYANOFORMATE

C-acylation of lithium enolates by methyl cyanoformate provides high yields of β keto esters under mild conditions and with 100percent regioselectivity.

Diels-Alder Reactions of 1-Alkoxy-1-amino-1,3-butadienes: Direct Synthesis of 6-Substituted and 6,6-Disubstituted 2-Cyclohexenones and 6-Substituted 5,6-Dihydropyran-2-ones

We report the cycloaddition reactions of 1-alkoxy-1-amino-1,3-butadienes. These doubly activated dienes are prepared on a multigram scale from crotonic acid chloride and its derivatives. The dienes undergo Diels-Alder (DA) and hetero-Diels-Alder (HDA) reactions under mild reaction conditions with a variety of electron-deficient dienophiles to afford cycloadducts in good yields with excellent regioselectivities. The hydrolysis of the DA cycloadducts provides 6-substituted and 6,6-disubstituted 2-cylohexenones, which are versatile building blocks for complex molecule synthesis. The corresponding HDA cycloadducts afford 6-substituted 5,6-dihydropyran-2-ones.

Physically mixed catalytic system of amino and sulfo-functional porous organic polymers as efficiently synergistic co-catalysts for one-pot cascade reactions

In this article, acid/base bi-functional polymeric materials were prepared using physically mixed porous poly(divinylbenzene-co-4-vinylbenzenesulfonic acid) (P(DVB-VBS)) with sulfonic acid groups and poly(divinylbenzene-co-4-vinylbenzyl amine) (P(DVB-VBA)) with amino groups, which were synthesized by solvothermal polymerization of crosslinker DVB with either phenyl 4-vinylbenzenesulfonate (PVBS) or 4-vinylbenzyl amine hydrochloride (VBAH) functional monomers together with subsequent hydrolyzation or alkaline treatment. The bi-functional polymeric materials were utilized as a synergistic catalytic system for one-pot cascade reactions including deacetalization-Henry condensation reaction, deacetalization-Knoevenagel condensation reaction and the transformation of 3,4-dihydropyran derivatives to α-ester cyclohexenone compounds. The crosslinked polymeric frameworks effectively isolated sulfonic acid and primary amine groups to ensure their roles as both acid and base catalyst simultaneously in a one-pot system. The hierarchical porosity of a physically mixed acid/base co-catalyst system provided the possibility for the multi-step transformation of more complex substrates.

Hollow Hyper-Cross-Linked Nanospheres with Acid and Base Sites as Efficient and Water-Stable Catalysts for One-Pot Tandem Reactions

A task-specific functionalized hyper-cross-linked polymer (HCP) with hollow spherical structure was synthesized by an easily accessible Friedel-Crafts reaction-based approach. A harmonious coexistence of acid (sulfonic acid) and base (amine) sites on a microporous organic material was achieved. The acid-base bifunctional HCP catalyst (HCP-A-B) structure was fully characterized by many physicochemical methods. In the subsequent tandem reactions (hydrolysis/Henry and hydrolysis/Knoevenagel reactions), the HCP-A-B catalyst displayed high catalytic efficiency and chemical stability toward water or organic solvent. These HCP-A-B catalyst characteristics led to the development of a previously unreported transformation of 2-ethoxy-3,4-dihydropyran derivative to a 2-cyclohexen-1-one derivative through a tandem reaction involving water-assisted ring-opening hydrolysis of the dihydropyran, an intramolecular aldol reaction, and a dehydration reaction. In all of these reactions, the bifunctional HCP-A-B catalyst can be recovered and reused more than 10 times without significant loss of activity.