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)

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]

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

Domains: Chemical Sciences; Catalysis; Chemical Sciences; Organic chemistry; Chemical Sciences; Medicinal Chemistry

Fanny Danton, Mohamed Othman, Ata Martin Lawson, Ján Moncol, Alina Ghinet, et al.. 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. Chemistry - A European Journal, 2019, 25 (24), pp.6113-6118. ⟨10.1002/chem.201901111⟩. ⟨hal-02563783⟩