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Synthesis and preliminary evaluation of some pyrazine containing thiazolines and thiazolidinones as antimicrobial

Chandrakant G Bonde1, Naresh J Gaikwad

  • 1Department of Pharmaceutical Sciences, Nagpur University Campus, Nagpur University, Amravati Road, Nagpur 440033, India. chandubonde@yahoo.co.in

Bioorganic & Medicinal Chemistry
|April 15, 2004
PubMed

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Basicity of Heterocyclic Aromatic Amines

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).
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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
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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.