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Synthesis of 1,4-Oxathiocines and Thiopyrans by the Reaction of 2-Amino-4,5-dihydro-3-thiophenecarbonitriles with Ethyl Diazoacetoacetate

✍ Scribed by Yamagata, Kenji ;Akizuki, Keiko ;Yamazaki, Motoyoshi

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The reaction of 4,5‐dihydro‐2‐(4‐morpholinyl)‐ or ‐2‐(1‐piperidinyl)‐ or ‐2‐(1‐pyrrolidinyl)‐3‐thiophenecarbonitriles 1a–i with ethyl diazoacetoacetate in the presence of rhodium (II) acetate dimer gave the corresponding ethyl 1,4‐oxathiocine‐3‐carboxylates 2a–f, h and acetyl(dihydro‐1‐thiophenylio)‐(ethoxycarbonyl)methanides 3a, b. Compounds 2a–f, h and 3a, b were heated at 140°C to give the corresponding ethyl thiopyran‐6‐carboxylates 4a–i in moderate to good yields.

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## Abstract Sulfonium ylides **1a‐h** reacted with sodium iodide to afford the corresponding thiopyrans **2a‐h.** On the other hand, compounds **1a‐d** were treated with thionyl chloride to give the ring opening products **3a‐d.** The reaction of compounds **3a‐d** with sodium iodide and triethylam

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✍ Hiroshi Maruoka; Kenji Yamagata; Motoyoshi Yamazaki 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v