80466-41-7Relevant academic research and scientific papers
A convenient method for the synthesis of 9-aryl-4-methoxynaphtho[2,3-c]furan-1(3H)-ones
Kobayashi, Kazuhiro,Kajimura, Yasuhiro,Maeda, Kouji,Uneda, Tomokazu,Morikawa, Osamu,Konishi, Hisatoshi
, p. 1593 - 1600 (2007/10/03)
A three-step procedure for the synthesis of the title lignan lactone derivatives is described. The route involves a tandem Michael addition/cyclization reaction between o-aroyl-α-methoxybenzyllithiums, which are generated in situ by the treatment of aryl
Sequential and regioselective Friedel-Crafts reactions of gem-dihalogenocyclopropanecarbonyl chlorides with benzenes for the synthesis of 4-aryl-1-naphthol derivatives
Nishii, Yoshinori,Tanabe, Yoo
, p. 477 - 486 (2007/10/03)
Novel, sequential and regioselective Friedel-Crafts type reactions of (E)-3-aryl-2,2-dihalogenocyclopropanecarbonyl chlorides 1 and 2,2-dichlorocyclopropanecarbonyl chlorides 3 with benzenes produce various 4-aryl-3-halogeno-1-naphthols 2 and 4-aryl-1-naphthols 4, respectively. One of the benzannulations involves the intramolecular cyclization of acid chlorides 1, followed by intermolecular coupling with substituted benzenes to give 4-aryl-3-halogeno-1-naphthols 2. As a demonstration of this annulation, 4-aryl-3-bromo-1-naphthols 2i and 2k are successfully converted into new analogues of 1-aryl-3-hydroxymethyl-4-methoxy-2-naphthoic acid lactones 13, a class of lignan lactones. The other benzannulation involves three series of reactions using acid chlorides 3a-c: (1) the intermolecular Friedel-Crafts acylation of 3 with one benzene molecule giving the intermediary 2,2-dichlorocyclopropyl(phenyl)-methanones 14a-c; (2) the intermolecular trapping of 14a-c with another benzene molecule accompanied by regioselective ring opening; and (3) the final intramolecular cyclization giving 4-phenyl-1-naphthols 4a-c. The use of p-xylene also gives the corresponding 4-(p-xylyl)-1-naphthol 4d. The reactions of alternatively prepared ketones 14 with benzenes gives a variety of 'unsymmetrically' substituted 4-aryl-1-naphthols 4c,e-k under identical conditions. However, the reaction using p-methoxyphenyl ketone analogues 14g does not produce 4-aryl-1-naphthols, but gives 5-aryl-2-(p-methoxyphenyl)-3-methylfurans 16. These annulations proceed straightforwardly (in a one-pot manner) and this variation is due to the highly regioselective cyclopropane ring-openings.
Sequential and regioselective Friedel-Crafts reactions of gem-dihalocyclopropanecarbonyl chlorides with benzenes for the synthesis of 4-aryl-1-naphthol derivatives
Nishii, Yoshinori,Tanabe, Yoo
, p. 8803 - 8806 (2007/10/02)
Two types of novel, sequential and regioselective Friedel-Crafts reactions of gem-dihalocyclopropanecarbonyl chlorides with benzenes proceeded in a one-pot manner; E-3-aryl-2,2-dihalo-cyclopropanecarbonyl chlorides reacted with substituted benzenes to afford 4-aryl-3-halo-1-naphthols, while 2,2-dichlorocyclopropanecarbonyl chlorides were transformed into 4-aryl-1-naphthols in benzene or p-xylene. Both annulations involved alternative and highly regioselective cyclopropane ring-openings.
The Synthesis of Model Lactones of Cyclolignan Type
Krepelka, Jiri,Holubek, Jiri
, p. 2123 - 2128 (2007/10/02)
Lactones VI-IX were prepared on reduction of anhydrides of 4-aryl-1-methoxynaphthalene-2,3-dicarboxylic acids IV and V with sodium borohydride in methanol.Catalytic hydrogenation on platinum of lactones VIII and IX gave lactones with hydrogenated ring A,
