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Phenyliodine(III) Diacetate/I2-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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| Authors: | Fanny Danton Dr. Mohamed Othman Dr. Ata Martin Lawson Dr. Ján Moncol Dr. Alina Ghinet Prof. Benoît Rigo Prof. Adam Daïch |
| Affiliation: | 1. Normandie Univ.;2. UNILEHAVRE, FR 3038 CNRS, URCOM, 76600 Le Havre, France. EA 3221, INC3M CNRS-FR 3038, UFR ST, BP: 1123, 25 rue Philipe Lebon, 76063 Le Havre Cedex, France;3. Department of Inorganic Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, 81237 Bratislava, Slovakia;4. Yncréa Hauts-de-France, HEI groupe d'Yncréa, Laboratoire de Pharmacochimie, 13 rue de Toul, 59046 Lille, France Inserm, U995-LIRIC, CHRU de Lille, Faculté de Médecine-Pôle Recherche Université Lille, 2 Place Verdun, 59045 Lille Cedex, France Faculty of Chemistry, Department of Organic Chemistry, “Al. I. Cuza” University of Iasi, Bd. Carol I nr. 11, 700506 Iasi, Romania;5. Yncréa Hauts-de-France, HEI groupe d'Yncréa, Laboratoire de Pharmacochimie, 13 rue de Toul, 59046 Lille, France Inserm, U995-LIRIC, CHRU de Lille, Faculté de Médecine-Pôle Recherche Université Lille, 2 Place Verdun, 59045 Lille Cedex, France |
| 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: | domino transformations Morin rearrangement oxidative methylene insertion thiazolidines thiazines |