Details

Autor(en) / Beteiligte

• Pham, Thuy Trang
• Chen, Xi
• Söhnel, Tilo
• Yan, Ning
• Sperry, Jonathan

Titel

Haber-independent, diversity-oriented synthesis of nitrogen compounds from biorenewable chitin

Ist Teil von

• Green chemistry : an international journal and green chemistry resource : GC, 2020-01, Vol.22 (6), p.1978-1984

Ort / Verlag

Cambridge: Royal Society of Chemistry

Erscheinungsjahr

2020

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• During drug discovery programmes, medicinal chemists rely on compounds derived from Haber ammonia as the source of this clinically important nitrogen heteroatom and as a result, the development of new pharmaceuticals is very energy intensive. Herein we report that biologically fixed nitrogen sourced from the biopolymer chitin can be readily incorporated into the diversity-oriented synthesis (DOS) of N-compounds relevant to drug discovery and development. The furfuryl alcohol derived from the chitin-sourced platform 3-acetamido-5-acetylfuran (3A5AF) undergoes a Piancatelli rearrangement to give a 3-aminocyclopentenone that is readily converted into a variety 4-aminocyclopentanones and 4-aminocyclopentene-1,3-diones. From two of these functionally rich bio-based platforms, structurally diverse, medicinally relevant N-scaffolds are attainable, including aminated Hajos-Parrish ketone (HPK) derivatives, aminated bicyclic ethers, bicyclic pyrrolidines, pyridines, isoquinolines and indoles. Thus, the DOS of compound libraries relevant to modern drug discovery programmes can be assembled independent of Haber ammonia. A chitin-sourced 3-aminocyclopentenone building block is an effective platform for the diversity-oriented synthesis of nitrogen compounds in processes independent of Haber ammonia.