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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
Author(s) -
Danton Fanny,
Othman Mohamed,
Lawson Ata Martin,
Moncol Ján,
Ghinet Alina,
Rigo Benoît,
Daïch Adam
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901111
Subject(s) - domino , regioselectivity , chemistry , combinatorial chemistry , methylene , medicinal chemistry , organic chemistry , catalysis
Abstract An efficient domino transformation using a phenyliodine(III) diacetate (PIDA)/I 2 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.