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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

6.1K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
6.1K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.9K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
2.9K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

2.9K
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
8.3K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.8K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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C-H functionalization of pyridines.

Susmita Maity1, Asish Bera1,2, Ayantika Bhattacharjya1

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|June 21, 2023
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Summary

Direct C-H functionalization of pyridine and piperidine is crucial for sustainable chemistry. This review explores methods to overcome pyridine

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Sustainable Chemistry

Background:

  • Pyridine and piperidine are vital nitrogen heterocycles in pharmaceuticals, natural products, and materials science.
  • Direct functionalization of pyridine is challenging due to its electron-deficient nature and nitrogen atom's coordinating ability.
  • Traditional synthesis relies on pre-functionalized acyclic precursors, often generating waste.

Purpose of the Study:

  • To review and summarize recent advancements in direct C-H functionalization of pyridine.
  • To highlight strategies addressing reactivity, regioselectivity, and stereoselectivity challenges.
  • To promote sustainable synthetic approaches in pyridine chemistry.

Main Methods:

  • Review of literature on direct C-H functionalization of pyridine.
  • Analysis of catalytic systems and reaction mechanisms.
  • Discussion of regiochemical and stereochemical outcomes.

Main Results:

  • Several catalytic systems enable direct C-H functionalization of pyridine with improved selectivity.
  • New methodologies overcome the inherent electronic and coordinating properties of pyridine.
  • Progress in achieving site-selective functionalization at various positions of the pyridine ring.

Conclusions:

  • Direct C-H functionalization offers a more sustainable and efficient route to functionalized pyridines.
  • Continued research is essential to expand the scope and applicability of these methods.
  • These advancements are critical for drug discovery and materials science.