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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 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
3.
The reaction of 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one with carbonyl compounds occurs at the C(6) and/or N(5) atoms depending on the nature of the reagent and the conditions. Condensation with aldehydes gives 6-arylidene-6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-ones.
Acylation using acid anhydrides or acid chlorides gave 5-acyl-, 6-acyl-, and 5,6-diacyl-5,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-ones
depending again on the reaction conditions. Acylation using chloroacetyl chloride is accompanied by an intramolecular alkylation
to give 7H,8H-2a, 7a-diaza-cyclopenta[f,g]naphthacene-1,7(2H)-dione. Phenyl isocyanate gave the derivative containing a CONHPh
group at position 6.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1509–1520, October, 2007. 相似文献
4.
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
5.
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
6.
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
7.
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
8.
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
9.
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
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.
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
12.
V. V. Dotsenko S. G. Krivokolysko B. P. Litvinov 《Chemistry of Heterocyclic Compounds》2007,43(5):599-607
The reaction of diketene with cyanothioacetamide in dry dioxane in the presence of triethylamine gives triethylammonium 3-cyano-6-methyl-4-oxo-1,4-dihydro-2-pyridinethiolate.
The regioselective S-alkylation of this thiolate is a convenient method for the preparation of substituted 4(1H)-pyridones
and also derivatives of thiazolo[3,2-a]pyridine and thieno[2,3-b]pyridine. The action of 2-amino-1,1,3-tricyanopropene on
this thiolate leads to its transformation into a new heterocyclic system, namely, 5H-pyrido[2′,3′:4,5]thiopyrano[2,3-b]pyridine;
treatment with iodine yields the oxidation product, namely, the corresponding bis(2-pyridyl) disulfide. The structure of isopropyl
(3-cyano-6-methyl-4-oxo-1,4-dihydro-2-pyridinyl)thioacetate was confirmed by X-ray diffraction structural analysis.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 716–725, May, 2007. 相似文献
13.
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
14.
L. M. Potikha N. V. Shkilna V. M. Kisil V. A. Kovtunenko 《Chemistry of Heterocyclic Compounds》2004,40(8):1052-1062
The alkylation of benzimidazo[1,2-b]isoquinolin-11(5H)-one has been studied. This occurs at N(5) or C(6) depending on the type of alkylating agent and the reaction conditions. It was shown that C(6) alkylation is effected in reactions with reactive alkyl halides. A repeat alkylation occurs preferentially at the same position. Interaction with o-xylylidene dibromide leads to spiro[benzimidazo[1,2-b]-isoquinolin-6,2'-indan]-11-one and 1,6-dihydro-11H-6a,11b-diazobenzo[b]benzo[5,6]cyclohepta[1,2,3-l,m]fluoren-11-one, which are derivatives of new heterocyclic systems. 相似文献
15.
B. Vigante G. Tirzitis D. Tirzite B. Chekavichus J. Uldrikis A. Sobolev G. Duburs 《Chemistry of Heterocyclic Compounds》2007,43(2):225-232
Different modifications of the Hantzsch synthesis using 10-methyl-10H-phenothiazine-3-carbaldehyde gave 4-(10-methyl-10H-phenothiazin-3-yl)-substituted
1,4-dihydropyridine-3,5-di-, 5-oxo-4,5-dihydro-1H-indeno[1,2-b]pyridine-, and 5,5-dioxo-4,5-dihydro-1H-5λ6-benzo[4,5]thieno[3,2-b]pyridine-3-carboxylic esters.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 280–288, February, 2007. 相似文献
16.
The Knoevenagel condensations of 5-[3-(trifluoromethyl)phenyl]furan-2-carbaldehyde with seven compounds containing an active
methyl or methylene group have been studied. The compounds used were: methyl 2-cyanoacetate, malononitrile, 2-furylacetonitrile,
acetophenone, 2-thioxo-1,3-thiazolidin-4-one (rhodanine), 5,5-dimethylcyclohexane-1,3-dione (dimedone), and methyl 2-azidoacetate.
The effect of microwave irradiation on the condensation reactions was studied and compared with “’classical”’ conditions.
Thermolysis of methyl 2-azido-3-{5-[3-(trifluoromethyl)phenyl]-2-furyl}propenoate afforded methyl 2-[3-(trifluoromethyl)phenyl)]-4H-furo[3,2-b]pyrrole-5-carboxylate.
(2E)-3-{ 5-[3-(Trifluoromethyl)phenyl]-2-furyl}propenoic acid was converted to the corresponding azide, which was cyclized
on heating into 2-[3-(trifluoromethyl)phenyl)]-4,5-dihydrofuro[3,2-c]pyridin-4-one. The latter after successive action of
POCl3 and NH2NH2-Pd/C gave 2-[3-(trifluoromethyl)-phenyl]furo[3,2-c]pyridine.
Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 825–831, June, 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.
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
19.
以取代苯甲醛、溴乙腈和6-苄基-3-硫代-3,4-二氢-1,2,4-三嗪-5(2H)-酮为起始原料,在超声辅助下,一锅合成了9个新型6-苄基-2-亚苄基-2H-噻唑[3,2-b][1,2,4]三嗪-3,7-二酮类化合物,结构经1H NMR,13C NMR和MS(ESI)表征并对其合成机理进行了初步研究。测试了目标化合物(4a~4i)的体外乙酰胆碱酯酶的抑制活性,其中4a和4d抑制活性最好,有进一步研究的价值。 相似文献
20.
I. V. Ukrainets N. L. Bereznyakova O. V. Gorokhova A. V. Turov 《Chemistry of Heterocyclic Compounds》2007,43(11):1426-1433
The bromination of 3-allyl-4-hydroxy-2-oxo-1,2-dihydroquinoline by molecular bromine is accompanied by the closure of a five
membered furan ring and gives the corresponding 2-bromomethyl-3,9-dihydro-2H-furo[2,3-b]quinolin-4-one.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1677–1686, November, 2007. 相似文献