79379-50-3

Usage

Type of compound

Heterocyclic aromatic compound

Derivation

Derived from pyrrole by substitution of an ethyl group at the 4-position and a phenyl group at the 2-position

Common uses

Synthesis of various pharmaceuticals and organic compounds, development of novel materials, precursor for the synthesis of heterocyclic compounds

Chemical reactivity

Versatile, able to participate in a range of chemical reactions

Biological activities

Potential activities have been studied, but exact pharmacological properties are not fully understood

Upstream product

• 81113-07-7 2-Ethyl-4-phenyl-2-trimethylsilanyloxy-but-3-ynenitrile 
• 14181-72-7 2-bromo-1-phenyl-ethanone oxime 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 183680-90-2 (4-Ethyl-2-phenyl-pyrrol-1-yl)-dimethyl-amine 
• 81112-99-4 3-Aminomethyl-1-phenyl-pent-1-yn-3-ol 
• 79379-53-6 5-Ethyl-6-morpholin-4-yl-3-phenyl-5,6-dihydro-4H-[1,2]oxazine 

Relevant academic research and scientific papers

New efficient, flexible and regioselective synthesis of 2,4-Di- and 2,3,4-trialkylated and arylated 1H-pyrroles

Starting from easily available 2-acetoxy aldehyde dimethylhydrazones rac-2, we prepared various alkyl- and aryl-substituted 1H-pyrroles 6 in good overall yield. The titanium-mediated a2-umpolung reaction of rac-2 with different acyclic and cyclic silyl enol ethers 3 leads directly or via 4-oxo hydrazones rac,anti-4 to 1-(dimethylamino)-1H-pyrroles 5. A novel method for the reductive removal of the dimethylamino group affording 1H-pyrroles 6 is presented. VCH Verlagsgesellschaft mbH, 1996.

Synthesis of Pyrrole Derivatives from 5,6-Dihydro-4H-1,2-oxazines via Reductive Deoxygenation by Use of Fe3(CO)12

α-Bromooximes such as α-bromoacetophenone oxime and ethyl 3-bromo-2-(hydroxyimino)propanoate react with enamines to give 5,6-dihydro-4H-1,2-oxazines in good yields.Dihydro-1,2-oxazine derivatives are also obtained by the reaction of α-bromooximes with vinyl ethers and silyl enol ethers in the presence of Na2CO3.Dihydro-1,2-oxazines can be converted into pyrrole derivatives via reductive deoxygenation by treating with Fe3(CO)12 in moderate to excellent yields.Iron carbonyl complexes other than Fe3(CO)12 are also effective for the pyrrole-forming reaction.The efficiency of the complexes for this reaction decreases in the or der: Fe3(CO)12 >> Et3NH > Fe2(CO)9 >> Fe(CO)5.Both of the dihydro-1,2-oxazine- and pyrrole-forming reactions can be carried out in a single flask, giving pyrrole derivatives in good yields.

PALLADIUM-CATALYZED SYNTHESIS OF PYRROLES

Pyrrole derivatives are prepared in high yields by the catalytic action of a Pd(II) salt on 1-amino-3-alkyn-2-ols which are obtained from conjugate ynones.

SYNTHESIS OF PYRROLE DERIVATIVES VIA DEOXYGENATION OF 4H-1,2-OXAZINES BY IRON CARBONYLS

The reaction of 5,6-dihydro-4H-1,2-oxazines, which are derived from α-bromooximes and enamines, with iron carbonyl complexes such as Fe3(CO)12 and (C2H5)3NH gives pyrrole derivatives in high yields, accompaning deoxygenation from the oxazines.