High Nucleophilicity of Cyclic Amidocarbene toward Aryl
Isocyanates, New Approach to Spiro[azetidinone-4,3‘-indolinone]
Derivatives
Ying Cheng
Bo Wang
Lan-Qing Cheng
10.1021/jo060265h.s003
https://acs.figshare.com/articles/dataset/High_Nucleophilicity_of_Cyclic_Amidocarbene_toward_Aryl_Isocyanates_New_Approach_to_Spiro_azetidinone_4_3_indolinone_Derivatives/3076552
The nucleophilic addition of β-lactam-4-ylidenes <b>2</b>, 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] <b>1 </b>in the presence of aryl isocyanates afforded both <i>N</i>-lactam and
<i>O</i>-lactam substituted spiro[azetidine-2-one-4,3‘-indole-2‘-one] derivatives <b>5</b> and <b>6</b> in the total yield of
65−86%. Upon hydrolysis, products <b>5</b> and <b>6</b> were converted into spiro[azetidine-2-one-4,3‘-indole-2‘-one] <b>9</b> that was analogous to known biologically active compounds.
2006-06-09 00:00:00
spiro
aryl isocyanates
ambiphilic cyclic amidocarbene