Five Membered Rings With One Heteroatom

Introduction to Heterocyclic Compound

All aromatic compounds are organic compounds. Most organic aromatic compounds that you have seen to date are six membered rings. These aromatic rings are called benzene rings comprising six carbon atoms with three double bonds in the structure. These compounds are called homocyclic compounds since all the atoms in the ring are the same. 

Heterocyclic compounds are those that have different atoms taking part in the formation of aromatic rings. There can be heterocyclic compounds- five membered rings with one heteroatom. The parent aromatic compounds that belong to this family of hydrocarbons are furan, pyrrole, and thiophene. The structures for each of these compounds are given below. 


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Structures of heterocyclic compounds- five membered rings with one heteroatom


Derivatives of Pyrrole Furan and Thiophene

There are different derivatives of the parent aromatic compounds consisting of five membered rings with one heteroatom. The saturated derivative of pyrrole is called pyrrolidine. Tetrahydrofuran is the saturated derivative of furan. Thiophene is the saturated derivative of thiophene. There are bicyclic derivatives of these parent aromatic compounds as well. They are indole (or isoindole for pyrrole), benzothiophene (for thiophene), and benzofuran (for furan).


Natural Occurrence of Such Heterocyclic Compounds

These heterocyclic compounds are present in the natural environment. The nitrogen-containing pyrrole is present in abundance in bone oil. This compound is formed upon the application of strong heat to the bones. The process of protein decomposition produces the aromatic compound due to strong heating.

Pyrrole rings are an integral component of different amino acids like proline and hydroxyproline. These amino acids form a major part of different proteins. Proline is considered as an essential amino acid. These proline and hydroxyproline-containing proteins are mainly found in high concentrations in collagen. Collagen is the chief structural constituent of skin, bones, ligaments, and tendons.


1. Natural Occurrence of Pyrrole Derivatives in Plants 

Pyrrole derivatives are also found naturally. They are an important part of different alkaloids. Plants produce alkaloids, which are a huge group of different organic alkaline nitrogen-containing compounds. For example, nicotine, produced by tobacco plants, is a well-known alkaloid that contains pyrroles. Some examples of such alkaloids are given below. 


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Different alkaloids containing heterocyclic rings

In plants, chlorophyll contains four pyrrole units joined together to form the porphyrin head, as observed in chlorophyll b.


2. Natural Occurrence of Pyrrole Derivatives in Animals

The chief constituent of our blood is hemoglobin. The heme group of hemoglobin is involved in transporting oxygen to different tissues of the body. The Heme group consists of a pyrrole ring. Similarly, myoglobin also contains a pyrrole ring in its structure. Vitamin B12 also contains pyrrole rings.

Porphyrin rings formed by the chain of four pyrrole rings are also found in bile pigments in the liver. One such bile pigment is bilirubin. It is the chief reason for the brownish-yellow color of our urine and feces. It is produced by the breakdown of heme obtained from dead and destroyed red blood cells.  


Natural Occurrence of Indole Derivatives

If we look at the indole derivatives that occur naturally, the first example will be phthalocyanines. They are synthetic pigments that consist of four isoindole rings linked together. One example of this group is the phthalocyanine blue. The commercial name of this compound is Monastral Fast Blue.

There are several plant and animal compounds that contain one or multiple indole units in their structure. One such example is vat dye indigo. It contains two indole rings. This product was previously obtained from plants. Now it is chemically synthesized on large scales. 

An important plant essential is indole-3-acetic acid. It promotes plant growth.

A closely related dye from animal species is Tyrian purple. This dye is obtained from snails. It was previously used during classical times. The chemical name of this compound is 6,6′-dibromoindigo. It has two bromine atoms bonded to 6 and 6’ carbon atoms.

Tryptophan is an essential amino acid in different organisms. It contains an indole ring in its structure. It is a constituent in several proteins that are involved in several vital processes. For example, the neurotransmitter serotonin, and Niacin, a B-complex vitamin, contain tryptophan. Serotonin is an essential regulator of human mood. Upon degradation, tryptophan produces Skatole, which can retain the indole ring. It is the major contributor to the strong odor found in mammalian feces. 

FAQs (Frequently Asked Questions)

1. What are the Commonly Observed Natural Products that Contain Indole Rings?

Ans: Indole is an essential constituent of several naturally occurring compounds. These compounds are involved in several biological processes. For example, Indole-3-acetic acid is an essential plant hormone required for its growth. It is also known as auxin. It promotes root growth, and therefore, plays an important role at the starting of plant growth. It continues to promote root growth throughout the life of the plant.


A commercially important plant product is vat dye indigo. It was previously obtained from indigo plants. Now it is chemically produced in industries. It contains two indole rings. A closely related dye to it is Tyrian purple, obtained from snails. It was used a long time ago. It contains two bromine atoms bonded to 6 and 6’ carbon atoms and hence called 6,6′-dibromoindigo.


The essential amino acid tryptophan also contains an indole ring. It is an important component of the neurotransmitter serotonin and Niacin, a B-complex vitamin.

2. What are the Commonly Observed Natural Products that Contain Pyrrole Rings?

Ans: Several natural products contain pyrrole rings. In humans, the heme group of hemoglobin contains a pyrrole ring. The heme group is associated with carrying oxygen to different tissues of the body. Myoglobin also contains a pyrrole ring.


Porphyrin rings composed of four pyrrole rings are found in bile pigments. Bile pigments are found in the liver and are responsible for the brownish-yellow color of our urine and feces. It is obtained by the breakdown of heme from dead red blood cells. One such bile pigment is bilirubin. Vitamin B12 also contains pyrrole rings.


The essential amino acid proline contains a pyrrole ring in its structure. Proline is an essential component of different important proteins like collagen. Collagen is the structural component of ligaments, bones, skins, and tendons.


Pyrrole derivatives are also found in plants. Plants produce several alkaloids, which contain pyrrole rings. One commonly known plant alkaloid is nicotine produced by the tobacco plant.