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The methodology proceeds under mild, operationally simple conditions and exhibits broad isocyanide scope, accommodating aryl, benzylic, aliphatic, and heterocyclic substituents to furnish a 19\u2010member library of benzothiazines in 51%\u201396% yields. The reaction demonstrates high functional\u2010group tolerance and scalability to the millimole level, enabling efficient access to structurally diverse benzothiazine derivatives relevant for medicinal chemistry exploration. Single\u2010crystal X\u2010ray diffraction analyses revealed characteristic conformational features of the scaffold, including a twisted\u2010boat geometry and a Z\u2010oriented arrangement of the two NH groups. In addition, late\u2010stage oxidation of the sulfur atom to the corresponding sulfone was readily achieved in high yield, highlighting the versatility of the scaffold for post\u2010assembly diversification. 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