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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
Author(s) -
Yamagata Kenji,
Akizuki Keiko,
Yamazaki Motoyoshi
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960513
Subject(s) - chemistry , dimer , ethyl acetate , medicinal chemistry , ethyl ester , stereochemistry , organic chemistry
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.