%0 Generic
%A Cheng, Ying
%A Wang, Bo
%A Cheng, Lan-Qing
%D 2006
%T High Nucleophilicity of Cyclic Amidocarbene toward Aryl
Isocyanates, New Approach to Spiro[azetidinone-4,3‘-indolinone]
Derivatives
%U https://acs.figshare.com/articles/dataset/High_Nucleophilicity_of_Cyclic_Amidocarbene_toward_Aryl_Isocyanates_New_Approach_to_Spiro_azetidinone_4_3_indolinone_Derivatives/3076543
%R 10.1021/jo060265h.s001
%2 https://acs.figshare.com/ndownloader/files/4782343
%K spiro
%K aryl isocyanates
%K ambiphilic cyclic amidocarbene
%X The nucleophilic addition of β-lactam-4-ylidenes 2, a type of ambiphilic cyclic amidocarbene, to aryl
isocyanates has been studied and their application in organic synthesis has been demonstrated. Thermolysis
of spiro[β-lactam-4,2‘-oxadiazolines] 1 in the presence of aryl isocyanates afforded both N-lactam and
O-lactam substituted spiro[azetidine-2-one-4,3‘-indole-2‘-one] derivatives 5 and 6 in the total yield of
65−86%. Upon hydrolysis, products 5 and 6 were converted into spiro[azetidine-2-one-4,3‘-indole-2‘-one] 9 that was analogous to known biologically active compounds.
%I ACS Publications