Sequential Hydroperoxylation and Amberlyst‐15 Catalyzed Hock‐type Rearrangement of Spiroepoxy/Spiroaziridine Oxindoles for the Synthesis of 2‐Hydroxybenzooxazin‐3(4H)‐ones

A sequential one‐pot direct strategy for the synthesis of 2‐hydroxy‐2‐substituted‐2H‐benzo[b][1,4]oxazin‐3(4H)‐ones is developed under ambient conditions with moderate to good yields (up to 75 %) by regioselective ring‐opening of spiro‐epoxy/aziridine oxindoles with 50 % aq. H2O2 followed by rearran...

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Veröffentlicht in:	Asian journal of organic chemistry 2024-02, Vol.13 (2)
Hauptverfasser:	Abu Saleh, S K, Ananda Shankar Mondal, Senapati, Swarup, Hajra, Saumen
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes Carbonyls Hydrogen peroxide Ketones Synthesis
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container_title	Asian journal of organic chemistry
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creator	Abu Saleh, S K Ananda Shankar Mondal Senapati, Swarup Hajra, Saumen
description	A sequential one‐pot direct strategy for the synthesis of 2‐hydroxy‐2‐substituted‐2H‐benzo[b][1,4]oxazin‐3(4H)‐ones is developed under ambient conditions with moderate to good yields (up to 75 %) by regioselective ring‐opening of spiro‐epoxy/aziridine oxindoles with 50 % aq. H2O2 followed by rearrangement reaction in presence of amberlyst‐15 catalyst. Further, sequential reaction with aldehydes/ketones and carbonyldiimidazole (CDI) gave spiro[benzo[b][1,4]oxazine‐2,4′‐[1,3]dioxolan]‐3(4H)‐ones and spiro[benzo[b][1,4]oxazine‐2,4′‐[1,3]dioxolane]‐2′,3(4H)‐diones, respectively.
doi_str_mv	10.1002/ajoc.202300581
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H2O2 followed by rearrangement reaction in presence of amberlyst‐15 catalyst. Further, sequential reaction with aldehydes/ketones and carbonyldiimidazole (CDI) gave spiro[benzo[b][1,4]oxazine‐2,4′‐[1,3]dioxolan]‐3(4H)‐ones and spiro[benzo[b][1,4]oxazine‐2,4′‐[1,3]dioxolane]‐2′,3(4H)‐diones, respectively.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.202300581</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Aldehydes ; Carbonyls ; Hydrogen peroxide ; Ketones ; Synthesis</subject><ispartof>Asian journal of organic chemistry, 2024-02, Vol.13 (2)</ispartof><rights>2024 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Abu Saleh, S K</creatorcontrib><creatorcontrib>Ananda Shankar Mondal</creatorcontrib><creatorcontrib>Senapati, Swarup</creatorcontrib><creatorcontrib>Hajra, Saumen</creatorcontrib><title>Sequential Hydroperoxylation and Amberlyst‐15 Catalyzed Hock‐type Rearrangement of Spiroepoxy/Spiroaziridine Oxindoles for the Synthesis of 2‐Hydroxybenzooxazin‐3(4H)‐ones</title><title>Asian journal of organic chemistry</title><description>A sequential one‐pot direct strategy for the synthesis of 2‐hydroxy‐2‐substituted‐2H‐benzo[b][1,4]oxazin‐3(4H)‐ones is developed under ambient conditions with moderate to good yields (up to 75 %) by regioselective ring‐opening of spiro‐epoxy/aziridine oxindoles with 50 % aq. 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H2O2 followed by rearrangement reaction in presence of amberlyst‐15 catalyst. Further, sequential reaction with aldehydes/ketones and carbonyldiimidazole (CDI) gave spiro[benzo[b][1,4]oxazine‐2,4′‐[1,3]dioxolan]‐3(4H)‐ones and spiro[benzo[b][1,4]oxazine‐2,4′‐[1,3]dioxolane]‐2′,3(4H)‐diones, respectively.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ajoc.202300581</doi></addata></record>
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subjects	Aldehydes Carbonyls Hydrogen peroxide Ketones Synthesis
title	Sequential Hydroperoxylation and Amberlyst‐15 Catalyzed Hock‐type Rearrangement of Spiroepoxy/Spiroaziridine Oxindoles for the Synthesis of 2‐Hydroxybenzooxazin‐3(4H)‐ones
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