42367-54-4

Upstream product

• 123-75-1 pyrrolidine 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 623-47-2 propynoic acid ethyl ester 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 

Downstream Products

• 1147864-01-4 ethyl 4-(diethoxyphosphoryl)-1-hydroxy-5-methyl-2-phenyl-1H-pyrrole-3-carboxylate 
• 1147864-13-8 ethyl 4-(diphenylphosphoryl)-1-hydroxy-5-methyl-2-phenyl-1H-pyrrole-3-carboxylate 

Relevant academic research and scientific papers

α-Cyclization of Tertiary Amines. Part 1.

A general diastereoselective synthesis of functionalised pyrrolidine, indolizidine, pyrrolizidine and its seven-, eirgth-membered homologues is reported, starting from readily available enamine esters and acetylenedicarboxylate (DMAD).

Consecutive Three-Component Coupling-Addition Synthesis of β-Amino Enoates and 3-Hydroxypyrazoles via Ethyl 3-Arylpropiolates

Two consecutive three-component syntheses furnishing β-amino enoates or 3-hydroxypyrazoles based upon the Sonogashira alkynylation of aryl iodides and ethyl propiolate were established in mostly excellent yields. The ethyl 3-arylpropiolate intermediates are Michael systems which are suited for concatenation with conjugate addition or cyclocondensation giving access to libraries of 21 different β-amino enoates and 17 different 3-hydroxypyrazoles. The rotational barrier of β-pyrrolidino enoates was assessed by studying the coalescence of pyrrolidinyl protons in VT-NMR spectra of electronically different substituted derivatives showing that the electronic substituent effect on the aryl group does not affect the height of the rotational barrier. This indicates that the substituents are essentially oriented orthogonally to the plane of the β-pyrrolidino enoates.

Tertiary 3-aminopropenones and 3-aminopropenoates: Their preparation, with and without Lewis acids, from secondary amines and 1,3-diketo compounds

A direct method for the preparation of tertiary 3-aminopropenones and 3-aminopropenoates from β-diketones and β-keto esters, and secondary amines has been developed. The reaction is performed without solvent in the presence or absence of Lewis acid as catalyst, depending on the reactivity of both the amine and the diketo substrate. Georg Thieme Verlag Stuttgart.