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Products from furans. VI. Synthesis of dihydro‐2‐disubstituted‐2 H ‐pyran‐3(4 H )‐ones, tetrahydro‐3‐(aminomethyl)‐2‐( p ‐methoxyphenyl)‐2‐methyl‐2 H ‐pyran‐3‐ol derivatives and 6‐( p ‐methoxyphenyl ‐6‐methyl‐7‐oxa‐1,3‐diazaspiro[4,5]decane‐2,4‐dione
Author(s) -
Georgiadis Minas P.
Publication year - 1986
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.5570230260
Subject(s) - chemistry , pyran , hydrogenolysis , ketone , stereochemistry , medicinal chemistry , organic chemistry , catalysis
Hydrogenolysis of 5,6‐dihydro‐6‐( p ‐methoxyphenyl)‐6‐methyl‐5‐oxo‐2 H ‐pyran‐2‐yl ethyl carbonate yielded dihydro‐2‐( p ‐methoxyphenyl)‐2‐methyl‐2 H ‐pyran‐3(4 H )‐one, 3 . Subsequently cyanohydrin 4 , derived from 3 , on reduction afforded 3‐(aminomethyl)tetrahydro‐2‐( p ‐methoxyphenyl)‐2‐methyl‐2 H ‐pyran‐3‐ol, 5 . The synthesis of N ‐dimethyl, N ‐isopropyl, N ‐imidazolyl as well as N ‐oxazolinyl derivatives of 5 is presented. The synthesis of 6‐( p ‐methoxyphenyl)‐6‐methyl‐7‐oxa‐1,3‐diazaspiro[4,5]decane‐2,4‐dione 10 , a spiro hydantoin prepared from ketone 3 is also reported.