Publication: Synthesis and Use of 2H-Azirin-3-amines as Dipeptide Synthons
Synthesis and Use of 2H-Azirin-3-amines as Dipeptide Synthons
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Breitenmoser, R. A., & Heimgartner, H. (2002). Synthesis and Use of 2H-Azirin-3-amines as Dipeptide Synthons. Helvetica Chimica Acta, 85, 885–912. https://doi.org/10.1002/1522-2675(200203)85:3<885::AID-HLCA885>3.0.CO;2-Z
Abstract
Abstract
Abstract
The synthesis of the new 2H-azirin-3-amines ('3-amino-2H-azirines') 11, 20, 28, and 33 as dipeptide synthons is described. The reactions of the starting amides with Lawesson reagent gave the corresponding thioamides, and consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO), and NaN3 led to the desired products. It is shown that these 2H-azirin-3-amines can conveniently be used as building blocks of the dipeptides Aib-(Me)Axx (Axx = alanine, valine), Aib-Homoproline, and Iva-Pro in the synthesis of several model pept
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- Breitenmoser, Roland A
- Heimgartner, Heinz
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Citations
Breitenmoser, R. A., & Heimgartner, H. (2002). Synthesis and Use of 2H-Azirin-3-amines as Dipeptide Synthons. Helvetica Chimica Acta, 85, 885–912. https://doi.org/10.1002/1522-2675(200203)85:3<885::AID-HLCA885>3.0.CO;2-Z
