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Synthesis and stereostructure of some spiro[morphinan‐6,2′(3′ H )‐[1,3,4]oxa(thia)diazolines]
Author(s) -
Somogyi László,
Szabó Zoltán,
Hosztafi Sándor
Publication year - 1995
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.1995199507188
Subject(s) - chemistry , thio , stereochemistry
Abstract Treatment of dihydrocodeinone (thio)semicarbazones 1a–d with Ac 2 O/ZnCl 2 afforded (6 S )‐spiro[morphinan‐6,2′(3′ H )‐[1,3,4]oxadiazolines] (2a, b) and (6 R )‐spiro[morphinan‐6,2′‐(3′ H )‐[1,3,4]thiadiazolines] (3a, b) , respectively. The structure of the products including the configuration of the spiro carbons was determined by 1 H‐ and 13 C‐NMR measurements.