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Unusual [3+2] Spiroannulation and Creation of Stereogenic Quaternary Center at C‐3 of Oxindole via Addition of (Het)arynes to Isomerized Morita‐Baylis‐Hillman Adduct of Isatin
Author(s) -
Meerakrishna Ramakrishnan Suseela,
Athira Mohanakumaran,
Shanmugam Ponnusamy
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201702356
Subject(s) - aryne , regioselectivity , chemistry , stereocenter , isatin , annulation , adduct , oxindole , reactivity (psychology) , indene , medicinal chemistry , stereochemistry , organic chemistry , catalysis , enantioselective synthesis , medicine , alternative medicine , pathology
A one‐pot synthesis of 1′‐methyl‐2′‐oxospiro [indene‐1, 3′‐indoline] and 3,3‐disubstituted 2‐oxindole derivatives in excellent combined yield by the reaction of methoxy isomerized MBH adducts of isatin with arynes and heteroarynes has been achieved. A plausible mechanism invoking a [3+2]‐spiro‐ annulation reaction and quenching the intermediate with proton is explained. Formation of regioselective products from unsymmetrical arynes is explained based on reactivity profiles of arynes/heteroarynes. Synthetic utility of synthesized compounds have been demonstrated.