- Reductive cleavage of benzannelated cyclic ethers and amines: Synthetic applications
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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.
- Azzena, Ugo,Demartis, Salvatore,Pilo, Luciano,Piras, Elisabetta
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- New one-pot synthesis of a benzonorcaradiene derivative by reduction of naphthalic anhydride with LiAlH4
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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.
- Wijsman, Geerlig W.,Van Der Veen, Lars A.,De Wolf, Willem H.,Bickelhaupt, Friedrich
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- The singular reduction of 1,8-bis-hydroxymethylnaphthalene to a benzonorcaradiene by LiAlH4
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Reduction of 1,8-naphthalic anhydride (1) with LiAlH4 in THF (or DME, but not Et2O) affords, in addition to diol 2, benzonorcaradiene 3. Extended treatment of 2 or lactone 4 also leads to 3, in 66% and 65% yield, respectively. Reduction of 4 with LiAlD4 established that formation of 3 proceeds via a symmetrical intermediate. No significant norcaradiene formation is observed upon comparable LiAlH4 treatment of 14,15,16 or 17. This novel reduction of a naphthalene derivative to a benzonorcaradiene appears to be unique to 2 or its precursors.
- Popovici-Mueller, Janeta V.,Spencer, Thomas A.
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- HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF
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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.
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Paragraph 00337; 00394
(2014/07/21)
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- METHODS FOR THE TREATMENT OF ALCOHOL ABUSE, ADDICTION AND DEPENDENCY
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The present invention is directed to methods for the treatment of alcohol abuse, addiction and / or dependency, alone and in combination with one or more anti-addiction agents.
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Page/Page column 18
(2008/12/06)
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- Reductive opening of 1H,3H-benzo[de]isochromene: Synthesis of 1,8-difunctionalised naphthalenes
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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.
- Foubelo, Francisco,Moreno, Benjamín,Yus, Miguel
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p. 4655 - 4662
(2007/10/03)
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- HYDROXY ALKYL SUBSTITUTED 1,3,8-TRIAZASPIRO[4.5]DECAN-4-ONE DERIVATIVES USEFUL FOR THE TREATMENT OF ORL-1 RECEPTOR MEDIATED DISORDERS
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The present invention is directed to novel hydroxy alkyl substituted 1, 3, 8-triazaspiro[4.5]decan-4-one derivatives of the general formula: wherein all variables are as defined herein, useful in the treatment of disorders and conditions mediated by the ORL-1 G-protein coupled receptor. More particularly, the compounds of the present invention are useful in the treatment of disorders and conditions such as anxiety, depression, panic, dementia, mania, bipolar disorder, substance abuse, neuropathic pain, acute pain, chronic pain migraine, asthma, cough, psychosis, schizophrenia, epilepsy, hypertension, obesity, eating disorders, cravings, diabetes, cardiac arrhythmia, irritable bowel syndrome, Crohn's disease, urinary incontinence, adrenal disorders, attention deficit disorder (ADD), attention deficit hyperactivity disorder (ADHD), Alzheimer's disease, for improved cognition or memory and for mood stabilization.
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