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Molecules 2005, 10(2), 367-375; doi:10.3390/10020367

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

Vienna University of Technology, Institute of Applied Synthetic Chemistry, Austria
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Received: 23 November 2004 / Accepted: 16 December 2005 / Published: 28 February 2005
(This article belongs to the Special Issue Sulfur-Nitrogen Heterocycles)
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Abstract

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. View Full-Text
Keywords: Hurd-Mori reaction; 1; 2; 3-thiadiazoles; thionyl chloride; plant activators; systemic acquired resistance. Hurd-Mori reaction; 1; 2; 3-thiadiazoles; thionyl chloride; plant activators; systemic acquired resistance.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Stanetty, P.; Turner, M.; Mihovilovic, M. 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 2005, 10, 367-375.

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