ISSN:
1434-4475
Keywords:
β-Ketoesters of indane-1-one and s-hydrindacene-1-one
;
Alkylation
;
2,2′-Spirobiindane-1-ones
;
Substituted 2,2′-spirobiindanes
;
1H-nmr spectra
;
Mass spectra
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Summary The spiroketones9, 16, and28 were prepared by cyclisation of the carboxylic acids7c, 13b, and25c and their acid chlorides, resp. (7d, 13c, and25d) with polyphosphoric acid (PPA) or SnCl4. The precursors of the latter compounds were synthesized by alkylation of the appropriate β-ketoester1 or2 with the “benzylchlorides”3 or4 with NaH inDMF. Subsequent hydrogenation with Pd/C led to the desired alkylated indane-esters. The chiral compounds11, 17, and31 were obtained by Friedel-Crafts acetylation. The chiral disubstituted 2,2′-Spirobiindanes22 and36 were prepared from the ketones20 and32/33 by catalytic reduction followed by Friedel-Crafts acetylation.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00810849
