A Short Review on Structures and Synthesis of some Heterocyclic Compounds

 

Mr. Azam Z. Shaikh*, Mrs. Harsha Jadhav*, Ms. Darshana M. Borse, Mr. Ritik. S. Jain

Department of Pharmaceutical Chemistry, VEW `S Ahinsa Institute of Pharmacy,

Dondaicha - 425408, Dist. Dhule, Maharastra India.

 

ABSTRACT:

It is a branch of chemistry dealing with the synthesis, properties and applications of this heterocycles. Its play a very important role in nature and in chemical synthesis as well. Heterocyclic chemistry deals with heterocyclic compounds which constitute about sixty-five percent of organic chemistry literature. A heterocyclic compound or rings structure is a cyclic compound contain atom of at least two different elements as a member of its ring. In nature N, O, S, containing heterocyclic molecule can be found in every living being. A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles. 59% of US FDA-approved drugs contain nitrogen heterocycles.

 

 

 

INTRODUCTION:

Heterocyclic compounds are of very much attention in our everyday life. Heterocyclic compounds have one or more hetero atoms in their structure. They might be cyclic or non-cyclic in nature. Heterocyclic compounds have an extensive range of application. They are mostly used as pharmaceuticals, as agrochemicals and as veterinarian products. They also discovery applications as sanitizers, designers, antioxidants, as corrosion inhibitors, as co-polymers, dye stuff. They are used as vehicles in the synthesis of other organic compounds. Some of the natural products e.g., antibiotics such as penicillin’s, cephalosporin; alkaloids such as vinblastine, morphine, reserpine etc. have heterocyclic moiety.^1,4

 

Heterocyclic compounds are broadly spread in nature and vital to life; they play a dynamic role in the metabolism of all living cells. Genetic material DNA in also collected of heterocyclic bases-pyrimidines and purines. An immense number of heterocyclic compounds, mutually synthetic and natural, are pharmacologically active and are in clinical use.^1,3

 

Heterocyclic compounds have a varied range of application: they are major between the type of compounds used as pharmaceuticals, as agrochemicals and as veterinarian products. They also find applications as sanitizers, designers, antioxidants, as corrosion inhibitors, as copolymers, dyestuff. They are used as vehicles in the synthesis of other organic   compounds.^1-4

 

 

Pyridine:

 

Description. Pyridine seems as a clear colourless to light yellow liquid with a penetrating nauseating odour. Density 0.978g/cm3. Flash point 68°F. Vapours are heavier than air.

 

Pyridine is used as a solvent and to make numerous different products such as medicines, vitamins, food flavorings, pesticides, paints, dyes, rubber products, adhesives, and waterproofing for fabrics. Pyridine can also be formed from the breakdown of many natural materials in the environment^7,8

 

Pyridine is a basic heterocyclic organic compound with the chemical formula C₅H₅N. It is structurally connected to benzene, with one methene group (=CH−) replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. Today it is synthesized on the scale of about 20,000 tons per year worldwide.^5,6,7,8

 

Furan

 

 

Description. Furan is a clear, colorless, flammable liquid cyclic ether with an ethereal odor. Furan is used as a transitional in the production of tetrahydrofuran, pyrrole and thiophene. Inhalation introduction to this substance causes eye and skin irritation and central nervous system depression. ^[10,11]

The Feist–Benary synthesis is a classic way to synthesize furans, while many syntheses have been established. One of the simplest synthesis methods for furans is the reaction of 1,4-diketones with phosphorus pentoxide (P₂O₅) in the Paal–Knorr synthesis. The thiophene formation reaction of 1,4-diketones with Lawesson's reagent also forms furans as side products. Many routes exist for the synthesis of substituted furans. ^[9,10,11]

 

Indole

 

Indole is an aromatic heterocyclic organic compound with formula C₈H₇N. It has a bicyclic structure, containing of a six-membered benzene ring fused to a five-membered pyrrole ring. Indole is extensively disseminated in the natural environment and can be produced by a variation of bacteria.^{12,13, ,17}

 

Indole-3-carbinol is a substance originate in vegetables such as broccoli, Brussels sprouts, cabbage, collards, cauliflower, kale, mustard greens, turnips, and rutabagas. It can also be produced in the laboratory. Indole-3-carbinol is used for prevention of breast cancer, colon cancer, and other types of cancer.^{12,13,14,15,16,17}

 

Pyrrole

 

Pyrrole is a colorless volatile liquid that blackens readily upon exposure to air, and is typically purified by distillation immediately before use. Pyrrole has a nutty odor. Pyrrole is a 5-membered aromatic heterocycle. The Substitution of pyrrole with alkyl substituents provides a more basic molecule—for example, tetramethyl pyrrole.

 

 

Synthesis:

Pyrrole is prepared industrially by treatment of furan with ammonia in the presence of solid acid catalysts, like SiO₂ and Al₂O₃. Pyrrole can also be formed by catalytic dehydrogenation of pyrrolidine.

 

Pyrrolidine

 

Pyrrolidine, also known as tetrahydropyrrole, is an organic compound with the molecular formula (CH₂)₄NH. It is a colorless liquid that is mixable with water and maximum organic solvents. It has a characteristic odor that has been described as "ammoniacal, fishy, shellfish-like.

 

Synthesis:

Pyrrolidine is prepared industrially by the reaction of 1,4-Butanediol and ammonia at a temperature of 165–200°C and a pressure of 17–21 MPa in the presence of a cobalt- and nickel oxide catalyst, which is supported on alumina.^18,19,20

 

The reaction is carried out in the liquid phase in a continuous tube- or tube bundle reactor, which is operated in the cycle gas method.^21,22

 

REFERENCES:

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2.     Jump up to: a b Thomas L. Gilchrist "Heterocyclic Chemistry" 3rd ed. Addison Wesley: Essex, England, 1997. 414 pp. ISBN 0-582-27843-0.

3.     Rees, Charles W. (1992). "Polysulfur-Nitrogen Heterocyclic Chemistry". Journal of Heterocyclic Chemistry. 29 (3): 639–651. DOI:10.1002/jhet.5570290306.

4.     Edon Vitaku, David T. Smith, Jon T. Njardarson (2014). "Analysis of The Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals". J. Med. Chem. 57: 10257-10274. DOI:10.1021/jm501100b. PMID 25255204.

5.     Kroehnke, Fritz (1976). "The Specific Synthesis of Pyridines and Oligopyridines". Synthesis. 1976 (1): 1–24. DOI:10.1055/s-1976-23941.

6.     Skell, P. S.; Sandler, R. S. (1958). "Reactions of 1,1-Dihalocyclopropanes with Electrophilic Reagents. Synthetic Route for Inserting a Carbon Atom Between the Atoms of a Double Bond". Journal of the American Chemical Society. 80 (8): 2024. DOI:10.1021/ja01541a070.

7.     Jones, R. L.; Rees, C. W. (1969). "Mechanism of heterocyclic ring expansions. Part III. Reaction of pyrroles with dichlorocarbene". Journal of the Chemical Society C: Organic (18): 2249. DOI:10.1039/J39690002249

8.     Gambacorta, A.; Nicoletti, R.; Cerrini, S.; Fedeli, W.; Gavuzzo, E. (1978). "Trapping and structure determination of an intermediate in the reaction between 2-methyl-5-t-butylpyrrole and dichlorocarbene". Tetrahedron Letters. 19 (27): 2439. DOI:10.1016/S0040-4039 (01)94795-1.

9.     Batsanov, A.; Howard, J.; Modal, R.; Steel, P. (2006). "The oxanorbornene approach to 3-hydroxy, 3,4-dihydroxy and 3,4,5-trihydroxy derivatives of 2-aminocyclohexanecarboxylic acid". Beilstein Journal of Organic Chemistry. 2 (9): 9. DOI:10.1186/1860-5397-29. PMC 1524792. PMID 16674802

10.  Katritzky, Alan R. (2003). "Synthesis of 2,4-disubstituted furans and 4,6-diaryl-substituted 2,3-benzo-1,3a,6a-triazapentalenes"2004 (2): 109. DOI:10.3998/ark.5550190.0005.208

11.  M. Tursky, L. L. R. Lorentz-Petersen, L. B. Olsen and R. Madsen, Org. Biomol. Chem., 2010, 8, 5576–5582

12.  https://pubs.rsc.org/en/content/articlehtml/2013/sc/c2sc21185h

13.  P. M. Jackson and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1990, 2156–2158.

14.  P. G. Gassman, T. J. van Bergen and G. Gruetzmacher, J. Am. Chem. Soc., 1973, 95, 6508–6509.

15.  M. Tursky, L. L. R. Lorentz-Petersen, L. B. Olsen and R. Madsen, Org. Biomol. Chem., 2010, 8, 5576–5582.

16.  Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. (1998). "Regioselective syntheses of substituted furans". Tetrahedron. 54 (10): 1955–2020. DOI:10.1016/S0040-4020(97)10303-9.

17.  Katritzky, Alan R. (2003). "Synthesis of 2,4-disubstituted furans and 4,6-diaryl-substituted 2,3-benzo-1,3a,6a-triazapentalenes" (2004 (2): 109. DOI:10.3998/ark.5550190.0005.208

18.  Armarego, Wilfred L. F.; Chai, Christina L. L. (2003). Purification of Laboratory Chemicals (5th ed.). Elsevier. p. 346.

19.  Harreus, Albrecht Ludwig. "Pyrrole". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. DOI:10.1002/ 14356007.a22_453

20.  Lubell, W.; Saint-Cyr, D.; Dufour-Gallant, J.; Hopewell, R.; Boutard, N.; Kassem, T.; Dörr, A.; Zelli, R. (2013). "1H-Pyrroles (Update 2013)". Science of Synthesis. 2013 (1): 157–388.

21.  Walsh, Christopher T.; Garneau-Tsodikova, Sylvie; Howard-Jones, Annaleise R. (2006). "Biological formation of pyrroles: Nature's logic and enzymatic machinery". Natural Product Reports. 23 (4): 517. DOI:10.1039/b605245m

22.  Pyrrolidine, The Good Scents Company

23.  Bou Chedid, Roland; Melder, Johann-Peter; Dostalek, Roman; Pastre, Jörg; Tan, Aik Meam. "Process for the preparation of pyrrolidine". Google Patents. BASF SE. Retrieved 5 July 2019.

 

 

Received on 28.01.2021                    Modified on 06.02.2021

Accepted on 12.02.2021                   ©AJRC All right reserved