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A Convenient 1,3‐Dipolar Cycloaddition Reaction for the Synthesis of Spirooxindoles and Some Other Spirocompounds Containing the 1,3,4‐Oxadiazole Moiety
Author(s) -
Alizadeh Abdolali,
Moafi Leila
Publication year - 2016
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201500515
Subject(s) - chemistry , isatin , oxadiazole , cycloaddition , moiety , 1,3 dipolar cycloaddition , yield (engineering) , proton nmr , carbon 13 nmr , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , materials science , metallurgy
A series of spiro[indoline‐3,2′‐[1,3,4]oxadiazol]‐2‐ones were prepared from the reaction of isatin derivatives and hydrazonoyl chlorides through the 1,3‐dipolar cycloaddition reaction. This method has some important aspects, such as mild reaction condition, easy purification, and high yield of products. Also, the synthesis of spiro[acenaphthylene‐1,2′‐[1,3,4]oxadiazol]‐2‐one and spiro[[1,3,4]oxadiazole‐2,9′‐phenanthren]‐10′‐one were studied under the same condition. The structures were confirmed spectroscopically (IR, 1 H‐ and 13 C‐NMR, and EI‐MS) and by elemental analyses. A plausible mechanism for this reaction is proposed.