Deconstructive Oxygenation of Unstrained Cycloalkanamines.
Angew Chem Int Ed Engl
; 59(10): 3900-3904, 2020 03 02.
Article
en En
| MEDLINE
| ID: mdl-31869508
ABSTRACT
A deconstructive oxygenation of unstrained primary cycloalkanamines has been developed for the first time using an auto-oxidative aromatization promoted C(sp3 )-C(sp3 ) bond cleavage strategy. This metal-free method involves the substitution reaction of cycloalkanamines with hydrazonyl chlorides and subsequent auto-oxidative annulation to in situ generate pre-aromatics, followed by N-radical-promoted ring-opening and further oxygenation by 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and m-cholorperoxybenzoic acid (mCPBA). Consequently, a series of 1,2,4-triazole-containing acyclic carbonyl compounds were efficiently produced. This protocol features a one-pot operation, mild reaction conditions, high regioselectivity and ring-opening efficiency, broad substrate scope, and is compatible with alkaloids, osamines, and peptides, as well as steroids.
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MEDLINE
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En
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Angew Chem Int Ed Engl
Año:
2020
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Article