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

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)
PDF Full-text Download PDF Full-Text [57 KB, uploaded 20 June 2008 16:49 CEST]
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.

Article Statistics

Load and display the download statistics.

Citations to this Article

Cite This Article

MDPI and ACS Style

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.

AMA Style

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(2):367-375.

Chicago/Turabian Style

Stanetty, P,; Turner, M.; Mihovilovic, M. 2005. "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 10, no. 2: 367-375.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert