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

Molecules

Peter Stanetty¹  Martin Turner² 

[1] id="af1-molecules-10-00367">Vienna University of Technology, Institute of Applied Synthetic Chemistry, Getreidemarkt 9/163-OC, A-1060 Vienna, Austri

关键词: Hurd-Mori reaction;    1;    2;    3-thiadiazoles;    thionyl chloride;    plant activators;    systemic acquired resistance;   

DOI  :  10.3390/10020367

来源: mdpi

【 摘 要 】

A route to methyl pyrrolo[2,3-d][1,2,3]thiadiazole-6-carboxylates as potential plant activators and inducers of systemic acquired resistance (SAR) is reported. A synthetic strategy based on cyclization of the thiadiazole ring system utilizing thionyl chloride via the Hurd-Mori protocol as key step was developed. Success of the ring closure reaction turned out to be highly dependent on the nature of the N-protecting group of the pyrrolidine precursor. While electron donors such as alkyl gave only poor conversion to the required 1,2,3-thiadiazoles, an electron withdrawing substituent such as methyl carbamate gave superior yields.

【 授权许可】

Unknown   
© 2005 by MDPI (http://www.mdpi.org).