Events The 2nd International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session b. Combinatorial Synthesis, Parallel Synthesis and Automation of the event The 2nd International Electronic Conference on Synthetic Organic Chemistry

Published date

01 Nov, 1998

Citation

Yonghan Fred Hu, Sylvie Baudart Baudart, Owen W. Gooding, Jeff W. Labadie, Wendy Miller, John A. Porco Jr., Parallel Synthesis of 1,2,3-Thiadiazoles Employing a "Catch and Release" Strategy, in Proceedings of The 2nd International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 1998, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-2-01689

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Parallel Synthesis of 1,2,3-Thiadiazoles Employing a "Catch and Release" Strategy

Yonghan Fred Hu ¹

Sylvie Baudart Baudart ¹

Owen W. Gooding ¹

Jeff W. Labadie ¹

Wendy Miller ¹

John A. Porco Jr. ¹

1. Argonaut Technologies, 887 Industrial Road, Suite G, San Carlos, CA 94070

Abstract

1,2,3-thiadiazoles were synthesized in parallel using a polymer sulfonyl hydrazide resin (PS-TsNHNH2) and employing a "catch and release" synthesis strategy. Resin capture of ketones synthesized from Weinreb amides and Grignard reagents afforded resin-bound sulfonylhydrazones. Cyclizative cleavage of supportbound sulfonylhydrazones with thionyl chloride afforded 1,2,3-thiadiazoles. Excess thionyl chloride was neutralized using liquid-liquid extraction cartridges.

Keywords

polystyrene sulfonylhydrazine resin

1,2,3-thiadiazole

"catch and release"

resin capture

Highly efficient and versatile Synthesis of Libraries of constrained b-strand Mimetics

Parallel Synthesis of Tertiary Amines using Polystyrene Sulfonylchloride (PS-TsCl) Resin