Details

Autor(en) / Beteiligte

• Nutt, Michael J.
• Annear, Jack W.
• Jones, Kieran D.
• Flematti, Gavin R.
• Moggach, Stephen A.
• Stewart, Scott G.

Titel

Dirhodium-Catalyzed Transannulation of N‑Sulfonyl-1,2,3-triazoles to 2,3-Dehydropiperazines

Ist Teil von

• Journal of organic chemistry, 2023-08, Vol.88 (16), p.11968-11979

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2023

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• The dirhodium­(II)-catalyzed synthesis of a range of C2-substituted 2,3-dehydropiperazines using 1-mesyl-1,2,3-triazoles and β-haloalkylcarbamates is reported. The reaction is proposed to proceed through an α-imino rhodium carbene 1,3-insertion into N–H followed by a base-mediated cyclization. C-Substituted dehydropiperazines can also be conducted directly from terminal alkynes in a three-step, one-pot operation, forming the triazole in situ. This methodology has also been expanded to afford several 2,5-disubstituted 2,3-dehydropiperazines as well as a larger 4,5,6,7-tetrahydro-1H-1,4-diazepine derivative.