1,2-Thiazines: One-Pot Syntheses Utilizing Mono and Diaza Analogs of Sulfones
Rebekka Anna Bohmann1, Yuto Unoh1,2, Masahiro Miura2
1Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany), Fax.
Abstract:
A one-pot Michael addition/cyclization/condensation reaction sequence for the regioselective synthesis of 1,2-thiazines, starting from propargyl ketones and NH-sulfoximines or NH-sulfondiimines, has been developed. Under mild and operationally simple reaction conditions previously unprecedented 1,2-thiazine 1-imide and 1-oxide derivatives are formed in good to excellent yields. The products represent heterocyclic building blocks, readily modifiable by a regioselective C-H bond functionalization, classical cross-coupling reactions, and deprotection.
Related Concept Videos
Preparation and Reactions of Sulfides
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Diazonium Group Substitution: –OH and –H
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism


