Síntese de indanos: uma seleção de métodos gerais e eficientes

Abstract

Recebido em 16/8/04; aceito em 1/10/04; publicado na web em 17/2/05 SYNTHESIS OF INDANS: A SELECTION OF GENERAL AND EFFICIENT METHODS. The indan ring system is present in several compounds with important pharmacological properties. In this account recent examples of selected methods (Friedel-Crafts acylation, cycloaddition reactions, ring contraction, cyclization and resolution) for the synthesis of indans are discussed.

Indatraline: Synthesis and Effect on the Motor Activity of Wistar Rats

“…The oxidation of 1,2-dihydronaphthalene 5 with iodine(III) [ 20 , 22 , 31 , 32 , 33 , 34 ] or with thallium(III) [ 30 , 31 , 33 , 35 , 36 , 37 , 38 , 39 , 40 ] in MeOH furnished the indane 4 , the naphthalene 7 and the addition product 8 , depending on the reaction conditions ( Table 1 ). With 0.9 equiv.…”

Hypervalent iodine reagents in the total synthesis of natural products

“…42,411,412 Ring contraction reactions can be effected by acids, bases, oxidants or by photochemical means. 412 The ring contraction of 1-alkyl-1,2-dihydronaphthalenes mediated by iodine(III) is an efficient method to obtain trans-1,3-disubstituted indanes, 413,414 representing an alternative to the analogous transformation mediated by thallium(III). [415][416][417] The exclusive formation of trans-1,3-disubstituted indanes in the ring contractions in methanol can be explained by the mechanism detailed in Scheme 93.…”

Iodine(III)-Mediated Ring Contraction of 1,2-Dihydronaphthalenes: Mechanistic Insight by Computational Investigations

“…Indanes constitute a benzene ring fused to a cyclopentane and are present in several designed molecules and natural products with remarkable biological properties . In this scenario, many approaches have been investigated to synthesize functionalized indanes . One of them is the ring contraction of 1,2‐dihydronaphthalenes promoted by thallium(III) or by iodine(III).…”