Studies on the Alkylation of Quinolin-2(1h)-one Derivatives
نویسندگان
چکیده
Alkylation of quinolin-2(1H)-one (1) and its C(6) and C(7) substituted dervatives (OMe, OBn, and Cl) with 2-bromoacetophenone or chloroacetone under basic condition (K2CO3 in DMF) gave a mixture of N1and O2alkylated products with the former one as a major product. However, alkylation of 8-methoxy-, 8-benzyloxy-, and 8-chloroquinolin-2(1H)-ones under the same reaction conditions gave exclusively O2-alkylated products.
منابع مشابه
Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents.
The reaction of 4-hydrazino-8-(trifluoromethyl)quinoline (2) with ethoxymethylenecyanoacetate afforded ethyl 5-amino-1-[8-(trifluoromethyl)quinolin-4-yl]-1H-pyrazole-4-carboxylate (3) and that with ethoxymethylenemalononitrile afforded 5-amino-1-[8-(trifluoromethyl)quinolin-4-yl]-1H-pyrazole-4-carbonitrile (5). Compounds 3 and 5 were hydrolyzed to get 5-amino-1-[8-(trifluoromethyl)quinolin-4-yl...
متن کاملSynthesis, Characterization and Antibacterial Activity of some Novel Thiosemicarbazides, 1,2,4-Triazol-3-thiols and their S-substituted Derivatives
The thiosemicarbazides 3a-c were appeared by reaction of the corresponding substituted hydrazides 1a-c with allylisothiocyanate 2. Synthesis of some novel 1,2,4-triazole-thiols 4a-c bearing a pyridyl unit using 1-(x-picolinoyl)-4-allyl-thiosemicarbazides (x = 2,3,4) in an alkaline solution, is reported. Also, the S-alkylation of triazole derivatives 5-7a-c is described. The structure of the syn...
متن کاملSynthesis, Antimicrobial and Antitubercular Activities of Some Novel Carboxamide Derivatives of 2-quinolones
A series of novel substituted N-(3-acetyl-2-oxoquinolin-1(2H)-yl)benzamide (AJQC1AJQC12) have been synthesized upon refluxing 3-acetyl-1-amino-quinolin-2-one and substituted benzoic acid in the presence of dry redistilled pyridine and silicon tetrachloride as coupling agent. 3-acetyl-1-amino-quinolin-2-one (AJQ1-AJQ12) were synthesized from substituted 3-acetyl coumarin upon refluxing with hydr...
متن کاملHow is the AIE mechanism profoundly changed in an ESIPT family: the novel introduction of a tetraphenylethene group onto (Z)-3-(quinolin-2-ylmethylene)-3,4-dihydroquinoxalin-2(1H)-one.
It is reported that two derivatives of (Z)-3-(quinolin-2-ylmethylene)-3,4-dihydroquinoxalin-2-(1H)-one (1) with a tetraphenylethene (TPE) group introduced at amide N atom of the dihydroquinoxalinone moiety (2) or at phenyl ring of the quinoline fragment (3) are synthesized, and the derivatives exhibit a remarkably enhanced aggregation-induced emission (AIE) activity than the parent. Although bo...
متن کاملSynthesis of 5-hydroxy-2,3,4,5-tetrahydro-[1H]-2-benzazepin-4-ones: selective antagonists of muscarinic (M3) receptors.
Two approaches to tetrahydro-[1H]-2-benzazepin-4-ones of interest as potentially selective, muscarinic (M(3)) receptor antagonists have been developed. Base promoted addition of 2-(tert-butoxycarbonylamino)methyl-1,3-dithiane with 2-(tert-butyldimethylsiloxymethyl)benzyl chloride gave the corresponding 2,2-dialkylated 1,3-dithiane which was taken through to the dithiane derivative of the parent...
متن کامل