%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