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1.
Interaction of 6,11-dihydro-13H-isoquino[2,3-b]quinazolin-13-one with alkylating agents occurs at two positions depending
on their nature and the reaction conditions-at C(6) or N(5). Fusion with methyl tosylate leads to 5-methyl-13-oxo-6,13-dihydro-11H-isoquino[3,2-b]quinazolin-5-ium salts, while interaction
with benzyl halides in the presence of i-PrONa gave 6-benzyl-and 6,6-dibenzyl-6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-ones.
Alkylation with olefins led to two types of products. In the case of maleinimides and maleic acid anhydride Michael adducts
at C(6) were formed and in the case of cyanocinnamic acid esters the reaction was accompanied by intramolecular acylation at N(5) to give 1-aryl-3,9-dioxo-3H,9H,11H-benzo[5,6][1,8]naphthyridino[1,8-ab]quinazoline-2-carbonitrile.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.11, 1698–1708, November 2007. 相似文献
2.
L. M. Potikha 《Chemistry of Heterocyclic Compounds》2007,43(6):759-768
The reaction of 3-haloanthranilic acids with o-bromomethylphenylacetonitrile gave 2-(2-carboxy-6-halophenyl)-1,4-dihydro-3(2H)-isoquinolinium
bromides. 2-Chlorophenylisoquinolinium bromides are readily converted into 4-R-6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-ones
by heating >145°C, but 2,4-dibromophenylisoquinolinium bromide only on fusing with anthranilic acid. The effect of the nature
and position of substituents in the quinazoline fragment of 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones on the rate of
the rearrangement into 6,11-dihydro-13H-isoquino[3,2-b]quinazol-13-ones has been studied. The oxidation and borohydride reduction
of 6,11-dihydro-13H-isoquino[3,2-b]quinazol-13-ones has been studied.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, 899–909, June, 2007. 相似文献
3.
L. M. Potikha V. A. Kovtunenko A. V. Tarasevich 《Chemistry of Heterocyclic Compounds》2007,43(12):1551-1558
Oxidation of the hydrobromide of 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one with dimethyl sulfoxide leads to 11-hydroxy-11H-isoquino[3,2-b]quinazoline-6,13-dione,
and with hydrogen peroxide to the hydrobromide of 2-[(4-oxo-3,4-dihydro-2-quinazolinyl)carbonyl]benzoic acid. Salts of 5-and
6-alkyl-substituted isoquino[3,2-b]quinazolines are readily oxidized on boiling in nitrobenzene, which leads to aromatization
of the isoquino[3,2-b]quinazoline system to 5-methyl-13-oxo-5H,13H-isoquino[ 3,2-b]quinazolinium perchlorate and 6-benzyl-13H-isoquino[3,2-b]quinazolin-13-one.
The structures of the dehydrogenation products were established from 1H NMR and UV spectra. The interaction of the obtained compounds with NaBH4 has been studied.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1833–1840, December, 2007. 相似文献
4.
L. M. Potikha R. M. Gutsul V. A. Kovtunenko G. G. Dubinina A. A. Tolmachev 《Chemistry of Heterocyclic Compounds》2008,44(5):585-593
It was shown that 6-acyl-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-ones are formed when 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one
is heated with the chlorides and anhydrides of carboxylic acids in the presence of bases (pyridine, NaOAc) while 5-acyl-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-ones
are formed in the presence of NaH. In the presence of NaH 6-acyl-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-ones form the
products from acylation and alkylation at position 5. The action of heat on 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one
in oxalyl chloride leads to 7H,8H-2a,7a-diazacyclopenta[fg]naphthacene-1,2,8-trione.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 741–750, May, 2008. 相似文献
5.
The direction of the reaction of anthranilic acids with o-bromomethylphenylacetonitrile upon fusion depends on the temperature
and nature of the substituent in the anthranilic acid. The reaction may lead to three types of products: Derivatives of 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones
below 150°C and to 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one or derivatives of 6H,12H,17H-dibenzo[3,4:6,7][1,8]naphthyridino[1,8-ab]quinazoline-6,17-diones
above 150°C depending on the nature of the substituent in the anthranilic acid. A study was carried out on the mechanism for
the formation of 6H,12H,17H-dibenzo[3,4:6,7][1,8]naphthyridino[1,8-ab]quinazoline-6,17-diones, which permitted the preparation
of 6-(4-methylphenyl)-6,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-one.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1059–1067, July, 2007. 相似文献
6.
L. M. Potikha R. M. Gutsul A. V. Turov V. A. Kovtunenko 《Chemistry of Heterocyclic Compounds》2008,44(2):208-213
Condensation of 2-(cyanomethyl)benzoic acid with 2-aminobenzylamine gave 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-11-one.
Its oxidation in nitrobenzene led to the formation of 5,13,5′,13′-hexahydro[6,6′]bi[isoquino[3,2-b]quinazoline]-11,11′-dione,
but in dichlorobenzene in the presence of elemental sulfur and iodine it gave the rearrangement product 6H-dibenzo[b,f][1,8]naphthyridin-5-one.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.2, 273–279, February, 2008. 相似文献
7.
L. M. Potikha V. A. Kovtunenko A. V. Tarasevich J. G. Wolf Ch. André 《Chemistry of Heterocyclic Compounds》2007,43(3):347-355
We studied the dependence of the direction of conversions for salts of angular 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-one
on temperature and the nature of the anion: heating in high-boiling solvents leads either to aromatization of the heterosystem
or to the rearrangement product, the linear 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one. When its hydrobromide is heated
in high-boiling solvents, along with dimerization of the linear isomers, processes of oxidation at the positions 6 and 11
of the heterosystem occur. The dimer obtained in the reaction with morpholine is readily cleaved, with formation of a 6-(4-morpholyl)-substituted
linear compound.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 430–439, March, 2007. 相似文献
8.
Heating 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one with isonicotinoyl chloride in pyridine gives 6-isonicotinoyl-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one. The 1-alkyl-4[(11-oxo-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-6-yl)carbonyl]pyridinium iodides obtained by alkylation of 6-isonicotinoyl-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one using alkyl iodides in the presence of NaH are converted to 1′-R-spiro[7H,8H-2a,7a-diazacyclopenta[fg]naphthacene-2,4′(1′H)-pyridine]-1,8(2H)-diones. The chemical and spectroscopic properties of the spiro compounds obtained
were studied.
For Communication 32 see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 52–58, January, 2009. 相似文献
9.
V. M. Kisil L. M. Potikha A. V. Turov V. A. Kovtunenko 《Chemistry of Heterocyclic Compounds》2008,44(2):214-224
The reaction of 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones with o-xylidene dibromide leads to 11-oxo-4bH,5H,10H,11H,16H-10a-aza-15b-azoniadibenzo[a,e]pleiadene
bromides, which are converted to 11-oxo-10H,11H,16H-10a-aza-15b-azoniadibenzo[a,e]pleiadene salts upon oxidation using nitrobenzene.
The reaction of these salts with benzylamine leads to 6-{2-[(benzylimino)methyl]phenyl}-7,12-dihydroisoquino[3,2-b][2]benzazepin-14(6H)-ones,
which recyclize to 11-oxo-5H,10H,11H-10a-aza-15b-azoniadibenzo[a,e]pleiadene perchlorates upon the action of perchloric acid.
The reactions of the 10a,15b-diazadibenzo[a,e]pleiadene salts obtained with NaBH4 were studied and the structures of the reduction products were determined by spectral methods.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 280–292, February, 2008. 相似文献
10.
The reaction of substituted anthranilic acids and esters with o-bromomethylphenylacetonitrile give 2,3-R,R1-7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-one hydrobromides. It was found that 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones
can exist in the two tautomeric imine and enamine forms. The tautomeric equilibrium position depends on the nature and position
of the substituent in the quinazoline fragment. The borohydride reduction, oxidation, and reaction of 2,3-R,R1-7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones with electrophilic reagents has been studied.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 562–573, April, 2007. 相似文献
11.
V. M. Kisel L. M. Potikha A. V. Turov V. A. Kovtunenko 《Chemistry of Heterocyclic Compounds》2001,37(9):1153-1161
Borohydride reduction in a series of 7-benzyl- and newly synthesized 7-arylmethylene-7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones leads stereoselectively to erythro-7-benzyl-6,6a,7,12-tetrahydro-5H-isoquino[2,3-a]quinazolin-5-ones. 7,7-Disubstituted 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones are inert to the action of sodium borohydride, but spiro[5H-isoquino[2,3-a]quinazolin-7(12H),2'-indane]-5-one is reduced under rigid conditions to 6,6a-dihydrospiro[5H-isoquino[2,3-a]quinazolin-7(12H),2'-indan]-5-one. 7-Acetyl- and 7-benzoyl-6,11-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones are converted in an aqueous alcoholic solution of sodium borohydride to the previously described 6,6a,7,12-tetrahydro-5H-isoquino[2,3-a]quinazolin-5-one. The structure and special features of the conformational behavior of the reduction products obtained were demonstrated by 1H NMR spectroscopy.! 相似文献
12.
L. M. Potikha V. M. Kisil A. V. Turov V. A. Kovtunenko 《Chemistry of Heterocyclic Compounds》2008,44(7):838-844
Treatment of 5-aryl-3-halo-12H-isoquino[2,3-a]quinazolines with electrophilic reagents readily forms their oxidation products.
Acylation of the 3-chloro-5-phenyl-7,12-dihydroisoquino[2,3-a]quinazolinium perchlorate with Ac2O in the presence of pyridine gave the product of electrophilic substitution at the C-7 atom 1-(3-chloro-5-phenyl-12H-isoquino[2,3-a]quinazolin-7-yl)-1-ethanone.
By the same route phenacyl bromides react with the anhydro base 1 to give 5-aryl-7-(2-aryl-2-oxoethyl)-3-halo-isoquino[2,3-a]quinazolin-13-ium bromides. These salts readily react with nucleophilic
reagents to form the products of addition at the C-12 atom.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1044–1052, July, 2008. 相似文献
13.
N. I. Mukarramov B. A. Urakov Kh. M. Shakhidoyatov 《Chemistry of Heterocyclic Compounds》2007,43(9):1210-1213
A study was carried out on the oxidative cyclocondensation of 2-thioxothieno-and 2-thioxopyrido[2,3-d]pyrimidin-4-ones. The
thiophene ring with excess π-electron density facilitates the reaction, while the pyridine ring with diminished π-electron
density hinders it. 2-Thioxothieno-[2,3-d]pyridimin-4-ones were converted into previously unreported 7H,13H-[1,2,4]thiadiazolo-[3,2-b:5,4-b′]bis(thieno[2,3-d]pyridimine-7,13-diones).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1424–1427, September, 2007. 相似文献
14.
V. N. Britsun A. N. Esipenko M. O. Lozinskii 《Chemistry of Heterocyclic Compounds》2005,41(6):782-786
The products of the reaction of 2-aryl-5-R-5,6-dihydro-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones with aryl bromomethyl ketones are 2-aryl-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones and aryl methyl ketones or 2,5-diaryl[1,3]thiazolo[3,2-b][1,2,4]triazoles and 3-phenyl-2-propenoic acid, depending on the structure of R. The reaction of 2-aryl-5-R-5,6-dihydro-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones with benzyl bromide yields 5-aryl-3-benzylthio-4H-1,2,4-triazoles and 3-aryl-2-propenoyl bromide.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 905–909, June, 2005. 相似文献
15.
3-[(E)-Arylmethylidene]-3,9-dihydropyrrolo[2,1-b]quinazolin-1(2H)-ones were prepared by reaction of quinazolyl-2-propionic acid
hydrochloride with aromatic aldehydes in acetic anhydride in the presence of Et3N. 3-[(E)-Arylmethylidene]-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-1-ols were formed by reduction of the 3-arylidene derivatives
with sodium borohydride in methanol, readily lost water when heated with acids, and were converted into 3-[(E)-arylmethylidene]-3,9-dihydropyrrolo[2,1-b]quinazolines.
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Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 463–467, September–October, 2006. 相似文献
16.
We have obtained a series of 3-aryl-7-arylidene-3,4-dihydro-2H-[1,3]thiazolo[3,2-a][1,3,5]triazin-6(7H)-ones by means of heterophase
aminomethylation of 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones with aqueous formaldehyde and aromatic amines in benzene or
toluene. We explain the effect of substituents in the heterocyclic substrate and the aryl amine on the efficiency of the process
within a detailed scheme for one of the possible aminomethylation reaction routes.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1095–1104, July, 2006. 相似文献
17.
The alkylation of 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-one proceeds at N(6) or C(–) depending on the type of alkylating agent and reaction conditions. C(–)-Alkylation occurs in the presence of base. The secondary alkylation of the 7-alkyl derivatives occurs at the same position under these conditions. Depending on the conditions, the reaction with o-xylylene dibromide leads to spiro[5H-isoquino[2,3-a]quinazolin-7(12H).2-indane]-5-one or 11-oxo-4b,5,10,16-tetrahydro-11H-10a-azonia-15b-azadibenz[a,e]pleiadene bromide, which are derivatives of new heterocyclic systems.Communication 8, see ref. [1].See also Letter to Editor [2].Taras Shevchenko Kiev University, 252017 Kiev, Ukraine. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 643–652, May, 2000. 相似文献
18.
V. N. Britsun A. N. Esipenko M. O. Lozinskii 《Chemistry of Heterocyclic Compounds》2006,42(5):693-697
3-Amino-2-thioxo-1,2,3,4-tetrahydroquinazolin-4-ones were converted into 2-aryl-5H-[1,3,4]thiadiazolo[2,3-b]quinazolin-5-ones
on treatment with carboxylic acids and POCl3. 3-Arylmethylidenamino-2-thioxo-1,2,3,4-tetrahydroquinazolin-4-ones also cyclized to 2-aryl-5H-[1,3,4]thiadiazolo[2,3-b]quinazolin-5-ones
when oxidized with potassium chlorate in acetic acid, but on heating they were deaminated to give 2-thioxo-1,2,3,4-tetrahydroquinazolin-4-one
and aryl nitriles.
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Translated from Khimiya Geteotsiklicheskikh Soedinenii, No. 5, 787–791, May, 2006. 相似文献
19.
Kumaresan Prabakaran 《合成通讯》2013,43(23):3528-3537
The reaction of 2,3,4,9-tetrahydro-1H-carbazol-1-ones with anthranilic acid in POCl3 yielded 7-chloro-5,6-dihydro-13H-indolo[3,2-c]acridines, while the same on reaction with isatin under the Pfitzinger reaction condition yielded 5,6-dihydro-13H-indolo[3,2-c]acridine-7-carboxylic acids. The latter reaction was carried out in different basic condition, because of, NaOH yielded more yield instead of KOH. Both the obtained products were treated with Pd/C in diphenyl ether to yield 13H-Indolo[3,2-c]acridines. 相似文献
20.
V. N. Britsun A. N. Esipenko M. O. Lozinskii 《Chemistry of Heterocyclic Compounds》2006,42(3):396-402
We have studied the reaction of 2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-one and 2-aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-ones
with amines, alkylating reagents, and hydrogen peroxide. We have shown that the presence of an aryl substituent at the 2 position
of [1,3-thiazino[3,2-a]benzimidazol-4-ones has a substantial effect on the direction of the reactions.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 445–452, March, 2006. 相似文献