Pyrrole

pyrrolespyrolepyrrolpyrrole ringpyrrolotetrapyrroledihydropyrrolePiloty–Robinson pyrrole synthesispyrrole derivativespyrrolium
Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C 4 H 4 NH.wikipedia
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Porphyrinogen

Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls.
In biochemistry a porphyrinogen is a member of a class of naturally occurring compounds with a tetrapyrrole core, a macrocycle of four pyrrole rings connected by four methylene bridges.

Heterocyclic compound

heterocyclicheterocycleheterocycles
Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C 4 H 4 NH.
1834: Runge obtains pyrrole ("fiery oil") by dry distillation of bones

Thiophene

thiophenesthienylThiophen
Pyrrole is a 5-membered aromatic heterocycle, like furan and thiophene.
Compounds analogous to thiophene include furan (C 4 H 4 O) selenophene (C 4 H 4 Se) and pyrrole (C 4 H 4 NH), which each vary by the heteroatom in the ring.

Porphyrin

porphyrinscoproporphyrinuroporphyrin
Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls.
Porphyrins are a group of heterocyclic macrocycle organic compounds, composed of four modified pyrrole subunits interconnected at their α carbon atoms via methine bridges (=CH−).

Porphobilinogen

Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme. ALA dehydratase catalyzes the condensation of two ALA molecules via a Knorr-type ring synthesis to form porphobilinogen (PBG).
The structure of the molecule can be described as molecule of pyrrole with sidechains substituted for hydrogen atoms at positions 2, 3 and 4 in the ring (1 being the nitrogen atom); respectively, an aminomethyl group \sCH2\sNH2, an acetic acid (carboxymethyl) group \sCH2\sCOOH, and a propionic acid (carboxyethyl) group \sCH2\sCH2\sCOOH.

Gertrude Maud Robinson

GertrudeGertrude Robinson
The starting materials in the Piloty–Robinson pyrrole synthesis, named for Gertrude and Robert Robinson and Oskar Piloty, are two equivalents of an aldehyde and hydrazine.
Gertrude Maud Robinson (formerly Walsh) was an influential organic chemist most famous for her work on plant pigments; the Piloty-Robinson Pyrrole Synthesis, which is named for her; her syntheses of fatty acids; and her synthesis of δ-hexenolactone, the first synthetic molecule with the character of penicillin.

Heme

haemheme grouphaeme
Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.
The enzymatic process that produces heme is properly called porphyrin synthesis, as all the intermediates are tetrapyrroles that are chemically classified as porphyrins.

Aromaticity

aromaticaromatic compoundaromatic ring
Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C 4 H 4 NH. Pyrrole is a 5-membered aromatic heterocycle, like furan and thiophene.
Other examples include pyridine, pyrazine, pyrrole, imidazole, pyrazole, oxazole, thiophene, and their benzannulated analogs (benzimidazole, for example).

Nitrogen

NN 2 dinitrogen
Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C 4 H 4 NH.
This may be offset by other factors: for example, amides are not basic because the lone pair is delocalised into a double bond (though they may act as acids at very low pH, being protonated at the oxygen), and pyrrole is not acidic because the lone pair is delocalised as part of an aromatic ring.

Knorr pyrrole synthesis

Knorr-type
ALA dehydratase catalyzes the condensation of two ALA molecules via a Knorr-type ring synthesis to form porphobilinogen (PBG).
The Knorr pyrrole synthesis is a widely used chemical reaction that synthesizes substituted pyrroles (3).

Friedlieb Ferdinand Runge

Friedlieb RungeF. F. RungeFriedrich Ferdinand Runge
Pyrrole was first detected by F. F. Runge in 1834, as a constituent of coal tar.
His chemical work included purine chemistry, the identification of caffeine, the discovery of the first coal tar dye (aniline blue), (Runge called aniline blue "Kyanol" (blue-oil)) coal tar products (and a large number of substances that derive from coal tar), paper chromatography, pyrrole, chinoline, phenol, thymol and atropine.

Furan

furansfuran ringFuranic
Pyrrole is a 5-membered aromatic heterocycle, like furan and thiophene.

Hans Fischer

Fischer, Hans
The syntheses of pyrrole-containing haemin, synthesized by Hans Fischer was recognized by the Nobel Prize.
Fischer's scientific work was mostly concerned with the investigation of the pigments in blood, bile, and also chlorophyll in leaves, as well as with the chemistry of pyrrole from which these pigments are derived.

Münchnone

Pyrroles bearing multiple substituents are obtained from the reaction of münchnones and alkynes.
The azomethine ylide reactivity of münchnones, and their reaction with alkynes in the synthesis of pyrroles, was first published by Huisgen et al.

Mucic acid

ammonium mucateD-galactarategalactarate
One synthetic route to pyrrole involves the decarboxylation of ammonium mucate, the ammonium salt of mucic acid.
The ammonium salt yields on dry distillation carbon dioxide, ammonia, pyrrol and other substances.

Indole

indolesindolicindol
Derivatives of pyrrole include indole, a derivative with a fused benzene ring.
It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring.

Polypyrrole

polypyrrolesPPYtetrapyrrole
Polypyrrole (PPy) is a type of organic polymer formed by the polymerization of pyrrole.

Tetrapyrrole

tetrapyrrolestetrapyrrolictetrapyrrolic structural frameworks
Tetrapyrroles are a class of chemical compounds that contain four pyrrole or pyrrole-like rings.

Simple aromatic ring

ringaromatic ringsheteroarene
Simple monocyclic aromatic rings are usually five-membered rings like pyrrole or six-membered rings like pyridine.

Pyrroline

pyrrolines3-pyrrolineC 4 H 5 N
Pyrroles can undergo reductions to pyrrolidines and to pyrrolines.
Pyrrolines are formally derived from the aromate pyrrole by hydrogenation.

Organic compound

syntheticorganicorganic compounds
Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C 4 H 4 NH.

Chemical formula

molecular formulaformulageneral formula
Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C 4 H 4 NH.

Carbon

Ccarbonaceouscarbon atom
Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C 4 H 4 NH.

Hydrogen

HH 2 hydrogen gas
Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C 4 H 4 NH.