Molecular Diversity of 1,3‐Dipolar Cycloaddition of Quinolinium Ylides with Isatylidene Malononitriles
- 21 November 2017
- journal article
- research article
- Published by Wiley in ChemistrySelect
- Vol. 2 (33) , 10835-10839
Abstract
Triethylamine promoted cycloaddition reaction of N‐ alkoxycarbonylmethylquinolinium bromide with isatylidene malononitriles afforded diastereoisomeric spiro[indoline‐3, 2′‐pyrrolo[1, 2‐ a ]quinolines] in satisfactory yields. The similar 1,3‐dipolar cycloaddition with N ‐( p ‐nitrobenzyl)quinolinlium bromide gave spiro[indoline‐3, 2′‐pyrrolo[1, 2‐ a ]quinolines] in good yields and with high diastereoselectivity. More importantly, the sequential cycloaddition reaction and oxidation reaction with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) resulted in novel 2‐(2‐oxoindolin‐3‐ylidene)‐2‐(2‐(dicyanomethylene)quinolin‐1‐yl)acetates.Keywords
Funding Information
- National Natural Science Foundation of China (21572196)
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