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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

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.
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Submitted on : Tuesday, May 5, 2020 - 3:50:48 PM
Last modification on : Thursday, July 2, 2020 - 3:29:22 AM

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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, Wiley-VCH Verlag, 2019, 25 (24), pp.6113-6118. ⟨10.1002/chem.201901111⟩. ⟨hal-02563783⟩

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