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Synthesis of alkyl 2-(bromomethyl)aziridine-2-carboxylates and alkyl 3-bromoazetidine-3-carboxylates as amino acid building blocks

✍ Scribed by Sven Mangelinckx; Asta Žukauskaitė; Vida Buinauskaitė; Algirdas Šačkus; Norbert De Kimpe

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
186 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

2-(Bromomethyl)aziridines 3-Bromoazetidines a b s t r a c t A short synthesis of alkyl 2-(bromomethyl)aziridine-2-carboxylates and alkyl 3-bromoazetidine-3-carboxylates was developed involving amination, bromination, and base-induced cyclization of alkyl 2-(bromomethyl)acrylates. These new small ring azaheterocyclic aand b-amino acid derivatives are promising synthons as demonstrated by their transformation to 2-(aminomethyl)aziridine-2-carboxylates and 3-aminoazetidine-3-carboxylates.

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✍ Petra Štefanič; Katja Turnšek; Danijel Kikelj 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 138 KB

A general synthesis of new alkyl 4-alkyl-2-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate peptidomimetic building blocks from the corresponding alkyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates through carbanion oxidation is described.