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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Syntheses of 1,3-Imidazoline-2-thione and 2-Phenylimino-1,3-thiazoline combinatorial libraries through different

Suyeal Bae1, Hoh-Gyu Hahn, Kee Dal Nam

  • 1Organic Chemistry Laboratory, Korea Institute of Science and Technology, Seoul 136-791, Korea.

Journal of Combinatorial Chemistry
|November 15, 2005
PubMed

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Preparation of 1° Amines: Azide Synthesis01:22

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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.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...