16200-50-3

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 33, p. 2169, 1968 DOI: 10.1021/jo01269a122

InChI:InChI=1/C12H19NO2/c1-5-9-8(4)13-11(10(9)6-2)12(14)15-7-3/h13H,5-7H2,1-4H3

Upstream product

• 6829-40-9 aminomalonic acid diethyl ester 
• 71703-50-9 3-ethyl-hexane-2,4-dione 
• 541-41-3 chloroformic acid ethyl ester 
• 6829-41-0 diethyl oximinomalonate 
• 4949-44-4 ethyl propanoylacetate 
• 69687-83-8 ethyl 3-ethyl-5-methyl-2-pyrrolecarboxylate 
• 123-63-7 paracetaldehyde 
• 123-54-6 acetylacetone 
• 107-87-9 2-Pentanone 
• 37013-86-8 ethyl 4-acetyl-3-ethyl-5-methyl-1H-pyrrole-2-carboxylate 

Downstream Products

• 59435-27-7 Benzyl 3,4-Diethyl-5-methylpyrrole-2-carboxylate 
• 98151-86-1 Benzyl 3,4-Diethyl-1,5-dimethylpyrrole-2-carboxylate 
• 1179588-16-9 ethyl 3,4-diethyl-5-methyl-1-(3,4,5-trimethoxybenzyl)-1H-pyrrole-2-carboxylate 
• 16200-52-5 3,4-diethyl-1H-pyrrole 
• 2683-82-1 2,3,7,8,12,13,17,18-octaethyl-porphyrin 
• 65858-42-6 2,3,7,8,12,13,17,18-octaethyl-5,15-diphenyl-21H,23H-porphyrin 
• 60188-33-2 2,3,7,8,12,13,17,18-octaethyl-5-phenylporphyrine 
• 270928-61-5 9-(2-methylbenzoyl)-3,4-dimethyl-7,8-diethyl-dipyrrinone 

Relevant academic research and scientific papers

Reduction of acyl pyrrole esters by zinc-hydrochloric acid

The pyrryl alkyl ketone and acetylpyrrole esters were reduced to corresponding alkylpyrrole esters by zinc-hydrochloric acid in alcohol in high yields (> 90%).

Stereochemistry and conformational analysis of hemirubin

Intramolecularly hydrogen-bonded analogs of the natural bile pigment, bilirubin, are very scarce. Nuclear Overhauser effect NMR studies of the newest analog, a hemirubin (1), confirms intramolecular hydrogen bonding and a ridge-tile-shaped conformation.

2,3-Diazaporphyrins Bearing Two Nitrogen Atoms at the Periphery

The first synthesis of 2,3-diazaporphyrins 3 bearing two nitrogen atoms at peripheral positions from tripyrranes 1, prepared in situ by mild acidolysis and decarboxylation of the di-t-butyldicarboxylates, and 4H-1,2,4-triazol-3,5-dicarbaldehyde (2) is described, using the [3+1] principle of porphyrine cyclization. Similar to the parent porphyrins, the new diazaporphyrins 3 exhibit significantly shielded inner protons, reflecting the ring current of an 18 ? aromatic system and Soret bands in the UV-vis. spectra with extinctions comparable to those of octaethylporphyrin.

Pyrrole Chemistry. An Improved Synthesis of Ethyl Pyrrole-2-carboxylate Esters from Diethyl Aminomalonate

Ethyl pyrrole-2-carboxylates, versatile precursors for the total synthesis of both synthetic model and naturally occurring tetrapyrroles and porphyrins, can be prepared in greatly improved yields by the addition of 1,3-diketones and preformed diethyl aminomalonate to boiling glacial acetic acid.The method is suitable for both small- and large-scale synthesis and has proved far more reliable than the original in situ dissolving zinc reduction of diethyl oximinomalonate discovered by Kleinspehn.Yields range from 60-70percent for the dominant product isomer from unsymmetrical diketones to 75-90percent for the single product derived from symmetrical diketones.Seventeen examples of alkyl-substituted ethyl pyrrole-2-carboxylates are provided.Improved procedures are given for the preparation of the required precursors.

Alkylation process

Substituted pyrrole compounds, such as 3-ethyl-4-methyl-5-carbethoxy pyrrole, 2,4-dimethyl-3-acetyl pyrrole and 2-methyl-5-carboxy pyrrole-4-propionic acid diethyl ester, are alkylated in a single step by reaction with an aldehyde or ketone in the presence of both an acid condensing agent such as hydriodic acid and a compatible reducing agent such as metallic zinc or stannous chloride. Suitable carbonyl reactants include formaldehyde, paraldehyde, isobutyraldehyde, acetone, cyclohexanone and methyl-isobutyl ketone. This application is a continuation application of U.S. application Ser. No. 281,624 filed Aug. 18, 1972, now abandoned, which is a continuation-in-part application of U.S. application Ser. No. 832,001, filed June 10, 1969, now abandoned.