10336-29-5Relevant articles and documents
Reductive cleavage of benzannelated cyclic ethers and amines: Synthetic applications
Azzena, Ugo,Demartis, Salvatore,Pilo, Luciano,Piras, Elisabetta
, p. 8375 - 8382 (2000)
Reduction of symmetrical intramolecular diarylmethyl ethers (3a and 8a) and amines (3b and 8b) with alkali metals in THF allows the generation of unsymmetrical oxy- or amino-functionalised arylmethyl organometallics. Such intermediates were successfully trapped with various electrophiles, allowing a new access to unsymmetrically 2,2'-disubstituted-1,1'-biaryls (5aa-5bf) and 1,8-disubstituted naphthalenes (10aa-10be). (C) 2000 Elsevier Science Ltd.
New one-pot synthesis of a benzonorcaradiene derivative by reduction of naphthalic anhydride with LiAlH4
Wijsman, Geerlig W.,Van Der Veen, Lars A.,De Wolf, Willem H.,Bickelhaupt, Friedrich
, p. 2095 - 2098 (1997)
Reaction of naphthalic anhydride (naphthalene-1,8-dicarboxylic anhydride) (1) or of 1,8-bis(hydroxymethyl)naphthalene (3) with LiAlH4 in refluxing THF yields the benzonorcaradiene derivatives 2 in yields of up to 50%. It is proposed that in the formation of this (strained) product an anti-hydroalumination reaction is involved, which is facilitated by the assistance of a neighbouring alkoxide function.
HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF
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Paragraph 00337; 00394, (2014/07/21)
Provided herein are heterocyclyl compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various neurological disorders, including but not limited to, psychosis and schizophrenia.
Reductive opening of 1H,3H-benzo[de]isochromene: Synthesis of 1,8-difunctionalised naphthalenes
Foubelo, Francisco,Moreno, Benjamín,Yus, Miguel
, p. 4655 - 4662 (2007/10/03)
The lithiation of 1H,3H-benzo[de]isochromene (6) with lithium and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 5% molar) in THF at -50°C gives dianionic intermediate 7, which by reaction with different electrophiles {H2O, D2O, tBuCHO, PhCHO, Me 2CO, (CH3CH2)2CO, [CH 3(CH2)4]2CO, (CH2) 5CO, (CH2)7CO, (-)-menthone} at the same temperature followed by hydrolysis leads to functionalised alcohols 8. If after addition of a carbonyl compound as the first electrophile [tBuCHO, (CH2)5CO, (-)-menthone], the resulting dialcoholate 9 is allowed to react at 0°C, a second lithiation takes place to give intermediate 10 which by reaction with a second electrophile [H2O, tBuCHO, (CH2)5CO, CO2], yields, after hydrolysis, 1,8-difunctionalised naphthalenes 11. Cyclization under acidic conditions of diols 8e-i gives oxygen-containing eight-membered heterocycles, which are homologous to the starting material 6.