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Regiocontrolled syntheses of some new spiro[polycyclic-1′-isothiochroman]-4′-one derivatives

✍ Scribed by Abdullah A. Al-Ahmadi; Maher F. El-Zohry

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
413 KB
Volume
7
Category
Article
ISSN
1042-7163

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✦ Synopsis

Indan-I-one (la), 1-tetralone (Ib), fluorenone (lc), and anthrone (Id) reacted with mercaptoacetic acid i n toluene in the presence of p-toluenesulfonic acid to give spiro[indan-1,2'-[l I, 3']oxathialan]-5'-one (2a), spiro[tetrahydro-naphthalene-l,2'-[1,3']oxathialan]-5'-one (2b), spiro[fluorene 9,2'-[1 I , 3']-oxathialan]-5'one (2c), and spiro[anthracene-9(1 OH)-2'-[1',3']-0xathialan]-5'-one (2d), respectively. Compounds 2a-d reacted with arenes in the presence of aluminum chloride to yield spiro[polycyclic-1'-isothiochrom- an]-4'-one derivatives 3a-t. The mechanisms of these reactions are discussed. All the synthesized spiroheterocyck derivatives were identified by conventional methods (IR, 'H-NMR spectroscopy) and elemental analyses.

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