Phenyliodine(III) Diacetate/I 2 ‐Mediated Domino Approach for Pyrrolo[1,4]Thiazines and 1,4‐Thiazines by a One‐Pot Morin Rearrangement of N,S ‐ Acetals

Fanny Danton; Mohamed Othman; Ata Martin Lawson; Ján Moncol; Alina Ghinet; Benoit Rigo; Adam Daïch

doi:10.1002/chem.201901111

Journal articles

Phenyliodine(III) Diacetate/I 2 ‐Mediated Domino Approach for Pyrrolo[1,4]Thiazines and 1,4‐Thiazines by a One‐Pot Morin Rearrangement of N,S ‐ Acetals

Fanny Danton ^{1, 2} Mohamed Othman ^{1, 2} Ata Martin Lawson ^{1, 2} Ján Moncol ³ Alina Ghinet ^{4, 5, 6} Benoit Rigo ^{5, 4} Adam Daïch ^{1, 2, *}

* Corresponding author

1 URCOM - Unité de Recherche en Chimie Organique et Macromoléculaire

2 INC3M - Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire

3 Slovak University of Technology in Bratislava

4 LIRIC - Lille Inflammation Research International Center - U 995

5 HEI - Hautes Etudes d’Ingénieur [Lille]

6 Alexandru Ioan Cuza University of Iași [Romania]

Abstract : An efficient domino transformation using a phenyliodine(III) diacetate (PIDA)/I2 combination towards Morin 1,4-thiazine compounds has been developed starting from N,S-acetals. The latter leads to "one-step" regioselective methylene insertion without the need for traditional sulfoxide intermediates in good yields. The reaction involves easily accessible N,S-acetals obtained from cost-effective basic ketones and cysteamine as starting materials. This process ultimately leads to 1,4-thiazines related to natural product and fused derivatives necessary for further QSAR study.

Keywords : Morin rearrangement domino transformations oxidative methylene insertion thiazines thiazolidines

Document type :

Journal articles

Domain :

Chemical Sciences / Catalysis

Chemical Sciences / Organic chemistry

Chemical Sciences / Medicinal Chemistry

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https://hal-normandie-univ.archives-ouvertes.fr/hal-02563783
Contributor : ADAM DAICH Connect in order to contact the contributor
Submitted on : Tuesday, May 5, 2020 - 3:50:48 PM
Last modification on : Tuesday, July 19, 2022 - 11:47:41 AM

Phenyliodine(III) Diacetate/I 2 ‐Mediated Domino Approach for Pyrrolo[1,4]Thiazines and 1,4‐Thiazines by a One‐Pot Morin Rearrangement of N,S ‐ Acetals

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Phenyliodine(III) Diacetate/I 2 ‐Mediated Domino Approach for Pyrrolo[1,4]Thiazines and 1,4‐Thiazines by a One‐Pot Morin Rearrangement of N,S ‐ Acetals

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