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 | Zendy

Meerakrishna Ramakrishnan Suseela | Zendy; Athira Mohanakumaran | Zendy; Shanmugam Ponnusamy | Zendy

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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.

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