title: [Synthesis of tert-butylcyclopentane-fused 1,3-oxazines and 1,3-thiazines].
abstract: Chlorosulphonyl isocyanate (CSI) addition to 4-tert-butylcyclopentene furnished the azetidinone (3) in a stereospecific reaction. Azetidinone 3 was transformed by ring opening esterification and lithium aluminium hydride (LAH) reduction to the 2-hydroxy-methyl-4-tert-butyl-1-cyclopentylamine (6). The N-methyl-aminoalcohol (8) was prepared from amino esters (5) with ethyl chloroformate and subsequent LAH reduction. By different ring-closure methods, a number of tert-butyl-cyclopentante-fused 1,3-oxazines and 1,3-thiazines were synthesized. A comparative study of the prepared compounds was performed by IR, 1H- and 13C-NMR, DEPT and DNOE measurements.
authors: Szent-Györgyi Albert Orvostudományi Egyetem, Gyógyszerészi Vegytani Intézet.
authors: G
authors: G
authors: Bernáth
authors: Z
authors: Z
authors: Szakonyi
authors: F
authors: F
authors: Fülöp
authors: P
authors: P
authors: Sohár
mesh_terms: D007202:Indicators and Reagents; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship; D013843:Thiazines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007202:Indicators and Reagents; D010078:Oxazines; D013843:Thiazines
vernacular_title: terc-Butil-ciklopentánnal kondenzált 1,3-oxazinok és 1,3-tiazinok szintézise.