108890-73-9Relevant academic research and scientific papers
Oxidative Cleavage of C2-C3 Bond in Isatin Using (Diacetoxyiodo)benzene: A Facile Synthesis of Carbamates of Alkyl Anthranilates
Kalbandhe, Amit H.,Kavale, Ashish C.,Thorat, Prerana B.,Karade, Nandkishor N.
supporting information, p. 763 - 768 (2016/03/12)
On reaction with (diacetoxyiodo)benzene, isatin and N-acetyl isatin undergo the oxidative C2-C3 bond cleavage to form carbamates of alkyl anthranilates and alkyl 2-acetamidobenzoate, respectively.
Quinazoline-2,4-dione derivative, and medical compositions for the prophylaxis and treatment of cranial nerve disease containing the same
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Page/Page column 10; 11, (2016/04/20)
The present invention relates to a novel quinazoline-2,4-dione derivative of formula (I), a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising a compound of formula (I) as an active ingredient for preventing or treating
Beyond conventional routes, an unprecedented metal-free chemoselective synthesis of anthranilate esters via a multicomponent reaction (MCR) strategy
Sarkar, Satavisha,Khan, Abu T.
supporting information, p. 12673 - 12676 (2015/08/06)
A hitherto unreported route for the synthesis of anthranilate esters is demonstrated using 2-nitrobenzaldehyde, malonitrile and an alcohol or amine via a metal and oxidant free multicomponent reaction (MCR) strategy. This process simultaneously installs an ester and urea or urethane functionality via CO and CN bond formations via concurrent oxidation of the aldehyde group and reduction of the nitro group involving an intramolecular redox process.
Zinc Triflate Catalyzed C-Benzylation: Chemo- and Regioselective Route to Amido Substituted Diaryl and Arylheteroarylmethanes
Deshmukh, Mahesh Subhashrao,Srivastava, Ananya,Das, Biswajit,Jain, Nidhi
, p. 10041 - 10048 (2015/11/03)
An unprecedented zinc triflate catalyzed selective C-benzylation of anilides and heteroaryl amides with benzyl chlorides having electron-donating group at para-position is reported. The protocol offers moderate to high yield of para-amido substituted diaryl and arylheteroarylmethanes, uses cheap and easily available benzyl chlorides as the benzylating agent, catalytic amount of zinc triflate, and takes place under ambient conditions. Aminodiarylmethane derivatives can be obtained by hydrolysis of the corresponding amides. The methodology has also been applied for preparing dimethoxydiarylmethanes in good yields, which are the key precursors for synthesis of phenolic natural products.
Reinvestigation of the synthesis of ketanserin (5) and its hydrochloride salt (5.HCl) via 3-(2-chloroethyl)-2,4-(1H,3H)-quinazolinedione (2) or dihydro-5H-oxazole(2,3-b)quinazolin-5-one (1)
Fakhraian, Hossein,Heydary, Mehdi
, p. 151 - 156 (2014/02/14)
The synthesis of ketanserin (5) and its hydrochloride salt (5.HCl) using respectively equimolar amounts of 3-(2-chloroethyl)-2,4-(1H,3H)-quinazolinedione (2) with 4-(parafluorobenzoyl)piperidine (3) and dihydro-5H-oxazole(2,3-b) quinazolin-5-one (1) with hydrochloride salt of 4-(parafluorobenzoyl)piperidine (3.HCl) is reinvestigated. The one-pot reaction of ethyl-2-aminobenzoate with ethyl chloroformate and ethanol amine has afforded 3-(2-chloroethyl)-2,4-(1H,3H) -quinazolinedione (2) (86%) that was then refluxed with 4-(parafluorobenzoyl) piperidine (3) in ethyl methyl ketone in the presence of sodium carbonate to obtain free base of ketanserin (87%). In another attempt, a very pure hydrochloride salt of ketanserin (5.HCl) was synthesized using equimolar amounts of dihydro-5H-oxazole(2,3-b)quinazolin-5-one (1) and hydrochloride salt of 4-(parafluorobenzoyl)piperidine (3.HCl) by a solvent-less fusion method. Thus, under optimized conditions, 180°C and a reaction time of 30 min, the powder mixture was transformed into glassy crystals that were initially readily soluble in chloroform but were transformed afterwards over time (2 h) to white precipitates (5.HCl) suspended in chloroform with a yield of 72%.
Effect of catalytic alkali metal bromide on Hofmann-type rearrangement of imides
Moriyama, Katsuhiko,Ishida, Kazuma,Togo, Hideo
supporting information; experimental part, p. 8574 - 8576 (2012/09/07)
The Hofmann-type rearrangement of aromatic and aliphatic imides using KBr as the catalyst proceeded to provide aromatic and aliphatic amino acid derivatives. We have also developed a new synthetic route to gabapentin with this method.
Hofmann-type rearrangement of imides by in situ generation of imide-hypervalent iodines(III) from iodoarenes
Moriyama, Katsuhiko,Ishida, Kazuma,Togo, Hideo
, p. 946 - 949 (2012/05/05)
The Hofmann-type rearrangement of aromatic and aliphatic imides using a hypervalent iodine(III) reagent generated in situ from PhI, m-CPBA, and TsOH·H2O proceeded in the presence of a base in alcohol to provide anthranilic acid derivatives and amino acid derivatives in high yields, respectively. This reaction proceeds through a tandem reaction via alcoholysis followed by a Hofmann rearrangement promoted by the formation of an imide-λ3-iodane intermediate.
N-substituted alpha-arylazacycloalkylmethanamines and their use as cardiovascular agents
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, (2008/06/13)
Novel compounds of the formula below wherein W is azetidine, pyrrolidine or piperidine, Q is a straight chain hydrocarbon radical of 1-4 carbons and may contain a double bond, and STR1 Ar is phenyl, pyridinyl or pyrimidinyl, a process for their preparation, and novel intermediates are disclosed. The novel compounds and the pharmaceutical compositions of this invention are useful in the treatment of hypertension, arrhythmias and angina.
Compounds having GABA like activity, and use of same in tissue irrigating solutions
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, (2008/06/13)
Compounds which enhance the efficiency of the corneal endothelial fluid pump thereby promoting normal corneal function and deturgescence of swollen corneas, and methods for the compounds' synthesis are described. In addition, surgical irrigating solutions
