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Updated: Jul 6, 2025
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Dearomative ipso-Cyclization to Spiropseudoindoxyls: An Extendable Approach To Access Indolo[3,2-c]quinolinones and
Chada Raji Reddy1,2, Agnuru Theja1,2, Ejjirotu Srinivasu1,2
1Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Abstract:
A metal-free oxidative intramolecular dearomative spirocyclization of indole-3-formyl-2-carboxamides has been developed for the first time, affording spiropseudoindoxyls in good yields. This domino process proceeds through sequential oxidation, decarboxylation and ipso-arylation. The unique feature of this approach includes the compatibility of N-protected-indole-2-carboxamides. Further, a hitherto unknown rearrangement of spiropseudoindoxyls to indoloquinolones has been achieved. The synthetic utility of this strategy has also been showcased by the construction of a natural alkaloid, isocryptolepine.
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