An improved synthetic approach to thieno[2,3-d]-1,2,3-thiadiazolecarboxylates via diazotization of aminothiophene derivatives
✍ Scribed by Peter Stanetty; Erwin Görner; Marko D. Mihovilovic
- Book ID
- 102341340
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1999
- Tongue
- English
- Weight
- 362 KB
- Volume
- 36
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
The common synthetic method for the synthesis of fused 1,2,3‐thiadiazoles via diazotization is not generally applicable to aminothiophenes. A substantially improved experimental protocol for the preparation of the title compounds as a potential inducer of systemic acquired resistance in plants is reported based on a novel cyclization mechanism via a Huisgen‐White type rearrangement.
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A Synthetic Approach to Methyl Thieno [2,3-d][1,2,3]thiadiazole Carboxylates via Diazotation. -A route to title compounds (VII) as highly potent inducers of systemic acquired resistance is reported. Cyclization towards the thiadiazole ring system is carried out using diazotation techniques. An alte
## Abstract Attempted hydrolysis of the ester of 3‐methoxycarbonyl‐1__H__‐thieno[2,3‐__e__][1,3,4]thiadiazine 4,4‐dioxide (**I**) under acidic conditions gave the ring‐contracted thieno[2,3‐__d__][1,2,3]thiadiazole (**V**) instead of the expected carboxylic acid. In addition to a discussion of the