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Synthesis of 3,4‐dihydro‐2 h ‐thiopyrans by the reaction of 4,5‐dihydrothiophenium‐1‐bis[ethoxy(and methoxy)carbonyl]methylides with sodium iodide
Author(s) -
Maruoka Hiroshi,
Yamagata Kenji,
Yamazaki Motoyoshi
Publication year - 2002
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570390131
Subject(s) - chemistry , sulfonium , thionyl chloride , sodium iodide , triethylamine , iodide , alkoxy group , medicinal chemistry , ring (chemistry) , sodium , methyl iodide , organic chemistry , chloride , alkyl , salt (chemistry)
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 triethylamine provided the corresponding thiopyrans 2a‐d.