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Synthesis of α-oxo-sulfines in the indole series

✍ Scribed by Jan Bergman; Ivan Romero

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
235 KB
Volume
47
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

magnified image Oxindole was found to react readily with thionyl chloride to give (in an excellent yield) the isolable sulfine (13a), which on heating (refluxing acetonitrile) gave isoindigo (15a). The dark violet 3‐sulfinato‐oxindole (13a) readily reacted with 2,3‐dimethylbutadiene to give a colorless cyclo‐adduct (14a). The sulfine also reacted readily with various nucleophilic reagents, thus, thioloacetic acid gave 3‐carboxymethylthiolo‐oxindole (23a). J. Heterocyclic Chem., (2010).

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The cycloaddition reaction of α-oxo sulf
The cycloaddition reaction of α-oxo sulfines and 2-trimethylsilyloxy-1,3-butadienes
✍ J. B. M. Rewinkel; B. Zwanenburg 📂 Article 📅 2010 🏛 Elsevier Science 🌐 English ⚖ 615 KB

## Abstract The cycloaddition reaction of α‐oxo sulfines with 2‐(trimethylsiloxy)‐1,3‐dienes, leading ultimately to thiacyclohexanone __S__‐oxides (alternatively named as thianone __S__‐oxides or perhydrothiapyranone __S__‐oxides) is described. 1‐Oxo‐2‐thioxo‐indane __S__‐oxide 2a, and several α‐ox