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Synthesis and X-ray Structure of a New Pyrrolo[1,2-b]-pyridazine Derivative
Molecules 2005, 10(2), 367-375; doi:10.3390/10020367
Article

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

* ,  and
Vienna University of Technology, Institute of Applied Synthetic Chemistry, Austria
* Author to whom correspondence should be addressed.
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.
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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