TY - JOUR
T1 - Brook Rearrangement as Trigger for Dearomatization Reaction
T2 - Synthesis of Non-Aromatic N-Heterocycles**
AU - Mondal, Rajarshi
AU - Agbaria, Mohamed
AU - Cohen, Orit
AU - Nairoukh, Zackaria
N1 - Publisher Copyright:
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
PY - 2024/1/11
Y1 - 2024/1/11
N2 - The [1,2]-Brook rearrangement stands as a potent technique for constructing complex molecules. In this study, we showcase its power in the dearomatization of aromatic N-heterocycles. Through a concise four-step process that integrates lithiation, nucleophilic addition, Brook rearrangement and dearomatization reaction, we demonstrate a versatile strategy for generating diverse non-aromatic N-heterocycles which exhibit ambident reactivities. Various acyl silanes, halo-pyridines, and quinolines have been explored within this context. The synthetic utility of this methodology is demonstrated through the construction of complex architectures.
AB - The [1,2]-Brook rearrangement stands as a potent technique for constructing complex molecules. In this study, we showcase its power in the dearomatization of aromatic N-heterocycles. Through a concise four-step process that integrates lithiation, nucleophilic addition, Brook rearrangement and dearomatization reaction, we demonstrate a versatile strategy for generating diverse non-aromatic N-heterocycles which exhibit ambident reactivities. Various acyl silanes, halo-pyridines, and quinolines have been explored within this context. The synthetic utility of this methodology is demonstrated through the construction of complex architectures.
KW - Brook rearrangement
KW - dearomatization
KW - heterocycles
KW - multicomponent reaction
KW - synthetic methods
UR - http://www.scopus.com/inward/record.url?scp=85177439443&partnerID=8YFLogxK
U2 - 10.1002/chem.202303588
DO - 10.1002/chem.202303588
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C2 - 37930139
AN - SCOPUS:85177439443
SN - 0947-6539
VL - 30
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 3
M1 - e202303588
ER -