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Lipunova, G. N.; Носова, Э. В.; Кодесс, М. И.; Charushin, Valery N.; Rozin, Yu. A.; Chasovskikh, O. M.

doi:10.1023/a:1012498322793

Cited by 9 publications

(8 citation statements)

References 2 publications

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“…A difference was observed in the multiplicities of the C 2 signal: it was a quartet of doublets in the spectrum of XIXb (J = 40.5, 3.5 Hz) and a doublet (J = 4.0 Hz) in the spectrum of XIXa. The coupling constant equal to 3.5-4.0 Hz may be assigned to inter- An additional support to structure XIX was obtained by studying intramolecular cyclization of 3-azolylamino-2-polyfluorobenzoylacrylates [17]. Furthermore, the 19 F NMR spectrum of cyclic compound XXIb should reveal coupling between 9-F and the trifluoromethyl group (an analogous interaction was discussed in [18]).…”

mentioning

confidence: 84%

Fluorine-Containing Heterocycles: XII. Fluorine-Containing Quinazolin-4-ones and Azolo[a]quinazolinone Derivatives

Lipunova¹,

Носова²,

Laeva³

et al. 2005

Russ J Org Chem

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Methods for the synthesis of fluorine-containing derivatives of 2-imino-1,3-diphenylquinazolin-4-one, imidazo[1,2-a]quinazolin-5-one, pyrazolo[1,5-a]quinazolin-5-one, and [1,2,4]triazolo[1,5-a]quinazolin-5-one were developed on the basis of the reaction of tetrafluorobenzoyl chloride with N,N'-diphenylguanidine and aminoazoles. * For communication XI, see [1].Fused quinazolin-4-one derivatives attract strong interest from the viewpoint of their potential biological activity. Antibacterial, antitoxoplasmatic, antihypertensive, and antihistaminic agents, phosphodiesterase inhibitors, and compounds possessing other kinds of biological activity have been revealed among quinazolin-4-one derivatives [2][3][4][5][6][7][8]. A known procedure for building up such heterocyclic systems is based on cyclization of 2-halo-substituted benzoyl chlorides with difunctional nitrogen-centered nucleophiles [4,[9][10][11]. This approach was not applied previously to the synthesis of fused imidazo-, pyrazolo[a]-and triazolo[a]-quinazolinones. There are published data only on the preparation of triazolo[a]quinazolinone derivatives via transformations of quinazolinones having a sulfanyl, hydrazino, thiosemicarbazido, or S-methylisothiosemicarbazido group in the 2-position [2,5,[12][13][14][15].In continuation of our studies on the synthesis of fused fluorine-containing nitrogen heterocycles, we have developed a general procedure for the preparation of fluorinated triazolo-, pyrazolo-, and imidazo[a]-quinazolinones by reaction of tetrafluorobenzoyl chloride with difunctional N,N'-dinucleophiles. By acylation of N,N'-diphenylguanidine (II) with tetrafluorobenzoyl chloride (I) in boiling toluene we obtained N, N'-diphenyl-N-(2,3,4,5-tetrafluorobenzoyl)-guanidine (III) (Scheme 1). The 1 H NMR spectrum of III confirmed the presence in its molecule of two

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mentioning

confidence: 84%

Fluorine-Containing Heterocycles: XII. Fluorine-Containing Quinazolin-4-ones and Azolo[a]quinazolinone Derivatives

Lipunova¹,

Носова²,

Laeva³

et al. 2005

Russ J Org Chem

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“…Cyclization of tetrafluorobenzoyl deriva tives 185a,c follows a different pathway leading to pyrazolo [1,5 a ]pyrimidines 187a,b (Scheme 58). 92 The synthesis of difluoro 1,2,4 oxadiazino[i,j] quinolone 188 involves cyclization of acrylate 189 in DMF in the presence of K 2 CO 3 (Scheme 59). …”

Section: Polyfluorobenzoyl Isothiocyanatesmentioning

confidence: 99%

Fluoroarenes in the synthesis of benzoannulated nitrogen-containing heterocycles

Layeva¹,

Носова²,

Lipunova³

et al. 2008

Russ Chem Bull

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“…Heating of ethyl 3-azolylamino-2-polyfluorobenzoyl acrylates 21 in acetonitrile in the presence of KF was shown to give the corresponding azolo[1,5-a]pyrimidines 22 (Scheme 8) [26].…”

Section: Other Fluorinated Benzazoles and Condensedmentioning

confidence: 99%

“…Indeed, the reactions of ethyl 3-ethoxy-2-polyfluorobenzoyl acrylates 36 (A = CF) with a variety of amines, hydrazines, or hydrazides followed by intramolecular cyclizations, hydrolysis of the ethoxycarbonyl group, and the displacement of fluorine atom at C-7 (Scheme 14) afford a variety of fluoroquinolones 39-43 [26,46,47].…”

Section: Fluorinated Benzazinesmentioning

confidence: 99%