Open AccessO-Cyclopropyl hydroxylamines: gram-scale synthesis and utility as precursors for N-heterocycles
Author(s) -
Kaitlyn Lovato,
Urmibhusan Bhakta,
Yi Pin Ng,
László Kürti
Publication year - 2020
Publication title -
organic and biomolecular chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.923
H-Index - 146
eISSN - 1477-0539
pISSN - 1477-0520
DOI - 10.1039/d0ob00611d
Subject(s) - chemistry , heteroatom , gram , combinatorial chemistry , sigmatropic reaction , stereochemistry , organic chemistry , ring (chemistry) , biology , bacteria , genetics
O-Cyclopropyl hydroxylamines, now accessible via a novel and scalable synthetic route, have been demonstrated to be bench-stable and practical precursors for the synthesis of N-heterocycles via a di-heteroatom [3,3]-sigmatropic rearrangement. In order to study the reactivity of these compounds in depth, a robust synthesis of both ring-substituted and ring-unsubstituted O-cyclopropyl hydroxylamines has been developed. Metal-free conditions for the facile N-arylation of these precursors were also identified. It was found that the N-arylated O-cyclopropyl hydroxamates can efficiently undergo a one-pot [3,3]-sigmatropic rearrangement/cyclization/rearomatization cascade under base-mediated conditions to furnish a structurally diverse set of substituted tetrahydroquinolines.