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Selenium-Containing Heterocycles from Isoselenocyanates: Synthesis of 1H-5-Selena-1,3,6-triazaaceanthrylene Derivatives

✍ Scribed by Plamen K. Atanassov; Anthony Linden; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2003
Tongue
German
Weight
157 KB
Volume
86
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The reaction of aryl isoselenocyanates 8 with methyl 3‐amino‐4‐chloro‐1‐ethylpyrrolo[3,2‐c]quinoline‐2‐carboxylate (6) in boiling pyridine leads to tetracyclic selenaheterocycles of type 9 in high yield (Scheme 3). A reaction mechanism via an intermediate selenoureido derivative A and cyclization via nucleophilic substitution of Cl by Se is proposed (Schemes 3 and 5). The reaction of 6 with 4‐bromophenyl isothiocyanate yields the analogous thiaheterocycle 12 (Scheme 4). The molecular structures of 9c and 12 have been established by X‐ray crystallography.

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Selenium-Containing Heterocycles from Is
Selenium-Containing Heterocycles from Isoselenocyanates: Synthesis of 1,3-Selenazinane and 1,3-Selenazinanone Derivatives
✍ Geoffroy L. Sommen; Anthony Linden; Heinz Heimgartner 📂 Article 📅 2007 🏛 John Wiley and Sons 🌐 German ⚖ 174 KB 👁 1 views

## Abstract The reaction of the intermediate ketene N,Se‐hemiacetal **3**, prepared from cyanomethylene derivatives **1** by treatment with Et~3~N and aryl isoselenocyanates **2**, with bis‐electrophiles **6, 7, 9**, and **11** in DMF affords tetrahydro‐1__H__‐1,3‐selenazine (=1,3‐selenazinane) der