[Synthesis of tert-butylcyclopentane-fused 1,3-oxazines and 1,3-thiazines].
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.
Bernáth
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G
Szent-Györgyi Albert Orvostudományi Egyetem, Gyógyszerészi Vegytani Intézet.
Szakonyi
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Z
Fülöp
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F
Sohár
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P
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
D007202:Indicators and Reagents; D010078:Oxazines; D013843:Thiazines
terc-Butil-ciklopentánnal kondenzált 1,3-oxazinok és 1,3-tiazinok szintézise.