Synthesis of 1,4,2‐benzodithiazine carboxylates via ring expansion reaction of 1,3‐benzodithioles

Abstract

A straight forward synthesis of the 1,4,2‐benzodithiazine system bearing an ester functionality as potential inducers of systemic acquired resistance in plants was developed utilizing the ring expansion reaction of 1,3‐benzodithioles. The structure of the isomers obtained was established using x‐ray diffraction. The reactivity of the products towards activated alkynes and ring contraction reactions in the presence of base is discussed.

Synthesis of substituted thieno[2,3-d]isothiazoles as potential plant activators

“…Both thieno [2,3-d] [1,2,3]thiadiazoles 4 [21][22][23][24][25][26] as well as thieno [3,2- 27 were prepared and the latter was identified as an alternative lead with comparable activity to compound 2. [21][22][23][24][25][26][27][28][29][30][31] Moreover, the benzene ring was also substituted by pyrrole leading to various pyrrolothiadiazoles (e.g., of type 6). 28,29 Further structural variations included compounds of type 8 30 and 9 31 .…”

Synthesis of Pyrrolo[2,3-d][1,2,3]thiadiazole-6-carboxylates via the Hurd-Mori Reaction. Investigating the Effect of the N-Protecting Group on the Cyclization

“…Recent efforts to find new heterocyclic systems based on the lead structure 2 [ 5 , 6 ] suggested the 1,2,3-thiadiazole system [ 7 ] as an integral motif for biological activity. Consequently, we became interested in modifying the benzo-part of Bion ® 2 , a strategy successfully applied in the development of biologically active thieno compounds 3 .…”