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One - pot synthesis of novel sulfur and selenium heterocycles by directed ortho-lithiation

✍ Scribed by S. W. Wright

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
37 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A procedure for the synthesis of benzo[e][1,3]thiazine‐2,4‐diones from benzamides by directed lithiation and sequential treatment with sulfur and phosgene is reported. Use of thiophosgene afforded 2‐thioxo‐2,3‐dihydro‐benzo[e][1,3] thiazin‐4‐ones. Application of this methodology to benzenesulfonamides afforded the previously unknown 1,1‐dioxo‐1,2‐dihydro‐1,4‐dithia‐2‐aza‐naphthalen‐3‐one ring system with phosgene and the 1,2‐dioxo‐2‐phenyl‐2,3‐dihydrobenzo[e][1,4,2]dithiazine‐3‐one ring system with thiophosgene. Use of selenium in place of sulfur afforded the novel analogous selenium heterocycles, however in the case of benzamides the use of selenium and phosgene afforded benzo[d]isoselenazol‐3‐ones unexpectedly.

📜 SIMILAR VOLUMES

ChemInform Abstract: One-Pot Synthesis o
ChemInform Abstract: One-Pot Synthesis of Novel Sulfur and Selenium Heterocycles by Directed ortho-Lithiation.
✍ S. W. Wright 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 26 KB 👁 2 views

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