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Synthesis of 1‐Substituted Pyrazolines by Reaction of Donor‐Acceptor Cyclopropanes with 1,5‐Diazabicyclo[3.1.0]hexanes
Author(s) -
Chagarovskiy Alexey O.,
Kuznetsov Vladimir V.,
Ivanova Olga A.,
Goloveshkin Alexander S.,
Levina Irina I.,
Makhova Ni.,
Trushkov Igor V.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900579
Subject(s) - chemistry , cyclopropane , substituent , annulation , bicyclic molecule , medicinal chemistry , lewis acids and bases , alkylation , alkyl , acceptor , ring (chemistry) , catalysis , organic chemistry , physics , condensed matter physics
Substituted pyrazolines were obtained by Ni(ClO 4 ) 2 · 6H 2 O‐catalyzed reaction of 1,5‐diazabicyclo[3.1.0]hexanes with donor‐acceptor cyclopropanes. The mechanism of this reaction includes alkylation of diaziridine nitrogen with Lewis acid‐activated donor‐acceptor cyclopropane followed by hydration of the formed 1,6‐zwitterionic intermediate and oxidation of pyrazolidine with air oxygen. This pathway is realized when starting bicyclic diaziridines have bulky alkyl substituent(s) at the C(6) atom preventing (3+3)‐annulation of two three‐membered rings.