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1.
A series of 4-substituted 3-(indole-3-yl)maleimides has been synthesized. Upon the action of CH3SO3H in TFA, the 3-(indole-3-yl)-4-(arylalkylamino)-maleimides undergo cyclization to give 12b,13-dihydro-4bH-indolo[3,2-d]pyrrolo[3,4-b][1]benzazepine-5,7(6H,8H)-dione derivatives. 相似文献
2.
V. F. Mironov L. M. Burnaeva Yu. Yu. Borisova A. T. Gubaidullin I. A. Litvinov G. A. Ivkova I. V. Konovalova 《Russian Journal of Organic Chemistry》2011,47(10):1521-1526
Reactions of 2-phenyl-4,4-bis(trifluoromethyl)-4,5-dihydro-1,3,2-benzodioxaphosphepin-5-one with 9,10-phenanthrenequinone
and dibenzoyl gave hydrolytically unstable spirophosphoranes with five- and seven-membered rings, 2-phenyl-4,4-bis(trifluoromethyl)-4,5-dihydrospiro[[1,3,2]benzodioxaphosphepine-2,2′-phenanthro[9,10-d][1,3,2]dioxaphosphol]-5-one and 2,4′,5′-triphenyl-4,4-bis(trifluoromethyl)-4,5-dihydrospiro[[1,3,2]benzodioxaphosphepine-2,2′-[1,3,2]dioxaphosphol]-5-one.
The structure of the first of these was proved by X-ray analysis. 相似文献
3.
S. M. Ramsh A. G. Ivanenko V. A. Shpilevyi N. L. Medvedskiy P. M. Kushakova 《Chemistry of Heterocyclic Compounds》2005,41(7):921-928
Alkaline hydrolysis of 3-tert-butyl-7,7-bis(hydroxymethyl)-3,4-dihydro-2H-thiazolo[3,2-a][1,3,5]-triazin-6(7H)-one can occur in three directions: with cleavage of the tetrahydrotriazine ring, with cleavage of the
thiazolidine ring, and also with opening of both rings. Depending on the process conditions, either the hydrolysis product
corresponding to the first direction or the hydrolytic decomposition products corresponding to the second and third directions
can be obtained in preparative quantities. Hydrolysis of 3,3′-di-tert-butyl-3′,4′-dihydro-2′ H-spiro[(perhydro-1,3-oxazine)-5,7′-thiazolo[3,2-a][1,3,5]triazin]-6′-one in (NH4)2CO3 solution occurs in two steps: in the first step, cleavage of the tetrahydrotriazine ring occurs; and in the second step,
opening of the perhydrooxazine ring occurs.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1089–1097, July, 2005. 相似文献
4.
Intramolecular cyclization reactions of 3,4-bis(indol-3-yl)maleimides 1, 3-(indol-1-yl)-4-(indol-3-yl)maleimides 2, and 3,4-bis(indol-1-yl)maleimides 3 under the action of protic acids were studied in order to estimate the parameters of the interaction between protonated and
unprotonated indole moieties. Geometric parameters, charge distributions, energy characteristics, and information concerning
the frontier orbitals of bisindolylmaleimides 1–3 were obtained from density functional B3LYP/6-31G(d) quantum chemical calculations. Alternative pathways of protonation of
bisindolylmaleimides with differently bonded indole and maleimide moieties were studied and pathways of cyclization of corresponding
conjugated acids leading to polyannelated compounds were analyzed. All the key intermediates of the cyclization reactions
correspond to stationary points on the potential energy surfaces (minima and transition states). Analysis of the potential
energy surfaces revealed almost linear dependences of the activation energies of the cyclization reactions under study on
the distances between the reaction centers, on the angle of approach of intramolecular electrophile, and on the energy gap
(energy difference between frontier orbitals). The key role in the cyclization reactions is played by structural similarity
between the starting indoleninium cations and the activated complexes of the reactions under study.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 754–760, May, 2006. 相似文献
5.
Belskaya N. P. Koksharov A. V. Deryabina T. G. Eltsov O. S. Slepukhin P. A. Bakulev V. A. 《Russian Chemical Bulletin》2010,59(4):833-837
Reactions of 2-arylazo-3-(1-azacycloalk-1-yl)-3-methylsulfanylacrylonitriles with male-imide in benzene gave octahydropyrrolo[3,4-a]pyrrolizines 2a–c, decahydro-2,7a-diaza-cyclopenta[a]indene 2e, and decahydro-5-oxa-2,7a-diazacyclopenta[a]indene 2f as a result of 1,3-dipolar cycloaddition. In a similar reaction with 3-allylsulfanyl-2-arylazo-3-(1-azacycloalk-1-yl)acrylonitriles
3, dipolar cycloaddition and intramolecular cyclization competed to give a mixture of compounds 2 (major products) and 1,4,6,7,8,8a-hexahydropyrrolo[2,1-c]-1,2,4-triazines 4b–d, 1,6,7,8,9,9a-hexahydro-4H-pyrido[2,1-c]-1,2,4-triazine 4e, and 1,4,6,7,9,9a-hexahydro-1,4-oxazino[3,4-c]-1,2,4-triazine 4f (minor products). 相似文献
6.
V. I. Potkin S. K. Petkevich P. V. Kurman 《Russian Journal of Organic Chemistry》2010,46(9):1305-1312
Acylation of thiophene and phenol with 3,4,4-trichloro-3-butenoyl chloride afforded the corresponding 1-(thien-2-yl)- and
1-(4-hydroxyphenyl)-3,4,4-trichloro-3-buten-1-ones, whose reaction with amines led to the formation of 3-amino-1-(thien-2-yl,
4-hydroxyphenyl)-4,4-dichloro-2-buten-1-ones The heterocyclization of the initial ketones into pyrazole structure was not
observed, and the reaction with hydrazine hydrate provided bispyrazole products, N,N′-bis(5-thien-2-yl)- and N,N′-bis[5-(4-hydroxyphenyl)-1H-pyrazol-3-ylmethylene]hydrazines. 相似文献
7.
Unusual reaction of 3,4-bis(3-nitrofurazan-4-yl)furoxan with ammonia,primary amines and hydrazine 总被引:1,自引:0,他引:1
Alexander A. Astrat’ev Dmitry V. Dashko Andrei I. Stepanov 《Central European Journal of Chemistry》2012,10(4):1087-1094
The nucleophilic displacement of two nitro groups in 3,4-bis(3-nitrofurazan-4-yl)furoxan with ammonia, primary aliphatic amines
and hydrazine leads to formation of a novel heterocyclic system, 7H-tris[1,2,5]oxadiazolo[3,4-b:3′,4′-d:3″,4″-f]azepine. The
reaction of compound 1 with secondary aliphatic amines proceeds in a typical way for nitrofurazans when the nitro-group in
the starting compound is substituted by RR’N-group.
相似文献
8.
Ivanov Yu. E. Stepanov D. E. Yavolovskii A. A. Shishkin O. V. D’yakonenko V. V. Kamalov G. L. 《Russian Journal of General Chemistry》2012,82(1):144-148
Dibenzimidazo crown ethers were synthesized by alkylation of α,ω-bis(benzimidazol-2-yl)alkanes and 1,2-bis(benzimidazol-2-ylsulfanyl)ethane
with tri- and tetraethylene glycol bis(4-toluenesulfonates). The structure of 6,7,9,10,12,13,21,22-octahydro[1,14,6,9,4,11]dioxadithiadiazacyclohexadecino[4,5-a:11,10-a′]dibenzimidazole was studied by X-ray analysis. 相似文献
9.
The alkylation of indole with the tridecanolide, pentadecanolide, and oxo lactones of ω-hydroxyethoxyundecanoic and ω-hydroxybutoxyundecanoic
acids was investigated. Higher indolylalkanoic acids, viz., ω-(3-indolyl)undecanoic, ω-(3-indolyl)tride-canoic, and ω-(3-indolyl)pentadecanoic
acids, were obtained. The scheme of the alkylation of indole with oxo lactones, and the difference in the rates of the reactions
of the ester and lactone bonds, were established from the reaction products.
See [1] for communication 119.
Translated from Khimiya Getetotsiklicheskikh Soedinenii, No. 2, pp. 216–217, February, 1980. 相似文献
10.
B3LYP/6-31G(d) density functional quantum chemical calculations of vicinally substituted bis(indol-1-yl)derivatives of 1,5-dihydropyrrol-2-one,
furan-2,5-dione, cyclopent-4-ene-1,3-dione, cyclobut-3-ene-1,2-dione, and pyrrolidine-2,5-dione were carried out to study
the effect of modification of the maleimide moiety in 3,4-bis(indol-1-yl)maleimides on the direction of intramolecular cyclization
under the action of protic acids. Geometric parameters, charge distributions, energy characteristics, and frontier orbital
energies of these compounds and the corresponding indoleninium cations were determined. Alternative protonation routes of
3,4-bis(indol-1-yl)-1,5-dihydropyrrol-2-one have been studied.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1348–1352, July, 2008. 相似文献
11.
2-Methylthiophene (1) was treated at 0°C with liquid bromine to form 3,5-dibromo-2-methylthiophene (2) which reacted with tributyl borate to give 2-methyl-3-bromo-5-boronate thiophene (3) at −78°C. Treatment of 3 with 3,4-difluorobrombenzene gave 2-methyl-3-bromo-5-(3,4-difluorophenyl)thiophene (4). Finally, a novel photochromic dithienylethene compound, 1,2-bis [2-methyl-5(3,4-difluorophenyl)-3-thienyl]perfluorocyclopentene
(DT-1), was synthesized by the reaction of 4 with perfluorocyclopentene at −78°C. The compound (DT-1) was characterized by IR, NMR, MS, elemental analysis and its photochromic behavior was also discussed.
__________
Translated from Chinese Journal of Organic Chemistry, 2007, 27(10): 1282–1284 [译自: 有机化学] 相似文献
12.
Ronald H. Rynbrandt 《Journal of heterocyclic chemistry》1974,11(5):787-790
1,2-Cycloaddition reactions of several enamines with N-substituted maleimides and 4-phenyl-1,2,4-triazoline-3,5-dione have been carried out. The adducts were transformed into 7-(substituted-amino)-3-azabicyclo[3.2.0]heptanes and a 1,2,4-triazolidine-1-acetaldehyde, respectively. These are the first reported examples of 3-azabicyclo[3.2.0]heptanes substituted in any position other than the 3-position. The reaction of an ynamine with N-benzylmaleimide afforded a bicyclic intermediate which upon hydrolysis gave a 2,5-dioxo-3-pyrrolidineacetic acid. 相似文献
13.
Peter Gajdoš Soňa Pavlíková Filip Bureš Alžbeta Krutošíková 《Central European Journal of Chemistry》2005,3(2):311-325
The synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (1a) are described. Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N-substituted products 1b-d. By hydrolysis of compounds 1a-c, the corresponding acids 2a-c were formed, or by reaction with hydrazine-hydrate, the corresponding carbohydrazides 3a-c were formed. By heating 2-[3-(trifluoromethyl)phenly]-4H-furo[3,2-b]pyrrole-5-carboxylic acid (2a) in acetic anhydride, 4-acetyl-2-[3-(trifluoromethyl)phenyl]furo[3,2-b]pyrrole (4) was formed. By hydrolysis of 4, 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole (5a) was formed, and reactions with methyl iodide or benzyl chloride gave N-substituted products 5b-c. The reaction of 4 with dimethyl butynedioate gave substituted benzo[b]furan 6. Compound 3a reacted with triethyl orthoesters giving 7a-c, which afforded with phosphorus (V) sulphide the corresponding thiones 8a-c. The thiones 8a-c reacted with hydrazine hydrate to form hydrazine derivatives 9a-c. The reaction of triethyl orthoformiate with compounds 9a-c led to furo[2′,3′: 4,5]pyrrolo[1,2-d][1,2,4]triazolo[3,4-f][1,2,4]triazines 10a-c. Hydrazones 11a-c were formed from 3a-c and 5-[3-(trifluoromethyl)phenyl]furan-2-carboxaldehyde. The effect of microwave irradiation on some condensation reactions
was compared with “classical” conditions. The results showed that microwave irradiation shortens the reaction time while affording
comparable yields. 相似文献
14.
L. M. Potikha R. M. Gutsul A. S. Plaskon V. A. Kovtunenko A. A. Tolmachev 《Chemistry of Heterocyclic Compounds》2011,47(3):342-354
The reaction of 3-NHR-isoquinolin-1(2H)-ones (R = Ar) with aromatic aldehydes in the presence of Me3SiCl or in acetic acid
leads to the formation of derivatives of dibenzo[b,f][1, 8]naphthyridin-5(6H)- one and benzo[f]isoquino[3,4-b][1, 8]naphthyridine-5,9(6H,7H)-dione.
The reaction for R = Het in the presence of Me3SiCl gives derivatives of 5H-pyrido[1',2':1,2]pyrimido[4,5-c]isoquinolin-5-one,
benzo[f]isoquinoline[3,4-b][1,8]naphthyridine-5,9[6H,7H]-dione, and derivatives of new heterocyclic systems, 5H-pyrazino[1',2':1,2]pyrimido[4,5-c]isoquinolin-5-one,
5H-[1,3]thiazolo[3',2':1,2]pyrimido- [4,5-c]isoquinolin-5-one, 5-H-benzo[f]pyrazolo[3,4-b][1,8]naphthyridin-5-one, and isoquino[3,4-b]-
[1,5]naphthyridin-5(6H)-one. The effect of the structure of substituent R and nature of the substituent in the benzaldehydes
on the structure of the reaction products was studied. 相似文献
15.
Alexander Y. Simonov Evgeny E. BykovSergey A. Lakatosh Yury N. LuzikovAlexander M. Korolev Marina I. ReznikovaMaria N. Preobrazhenskaya 《Tetrahedron》2014
15, 16, and 17-Membered lactones based on the bis-3,4(indol-1-yl)maleimide framework were obtained using intramolecular esterification reaction starting from 3-(1-ω-carboxyalkyl-2,3-dihydroindol-1-yl)-4-(1-ω-hydroxyalkyl-2,3-dihydroindol-1-yl)-maleimides. 3,4-Dibromo-maleimide, ω-(2,3-dihydroindol-3-yl)alkanoic acids, and ω-(2,3-dihydroindol-3-yl)alkanoles were used as starting compounds. Substitution of Br for the substituted indolines followed by the intramolecular cyclization of O-silylated hydroxyl acids derivatives led to macrolactones that incorporated 4-(dihydroindol-1-yl)-3-(indol-1-yl)maleimide moieties. Indoline nuclei in these compounds were dehydrogenated by DDQ in refluxing toluene to give 15, 16 or 17-membered lactones 3-[(ω-3-carboxyalkylindol-1-yl)-4-(ω-hydroxyalkylindol-1-yl)maleimides. Quantum chemical calculations showed that the formation of macrolactones of smaller size (13-membered) corresponds to the higher Gibbs energy ΔG# and correlates with the absence of the target reaction product. 相似文献
16.
I. E. Tolpygin 《Russian Journal of Organic Chemistry》2012,48(1):104-108
A number of 2-(anthracen-9-yl)-substituted imidazolidines and hexahydropyrimidines were synthesized by reaction of N,N′-bis[aryl(hetaryl)methyl]ethylene-1,2-diamines and N,N′-bis[aryl(hetaryl)methyl]-propane-1,3-diamines with anthracene-9-carbaldehyde. The obtained compounds showed chemosensor
activity toward Cd2+, Cu2+, and Hg2+ ions. 相似文献
17.
E. O. Chukhajian A. A. Khachatryan A. R. Gevorkyan H. A. Panosyan 《Chemistry of Heterocyclic Compounds》2009,45(4):426-429
In aqueous base medium p-bis{3-[N-(3-chlorobuten-2-yl)pyrrolidinio (piperidinio or morpholinio)]-propyn-1-yl}benzene dichlorides undergo a two-way
dehydrochlorination-cyclization reaction to form benzo[5,6-a:5′,6′-c]bis(2,2-tetramethylene- or -2,2-pentamethylene-4-methylisoindolinium) and benzo-[5,6-a:5′,6′-c]bisspiro(4-methylisoindoline-2,4′-morpholinium) dichlorides.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 546–549, April, 2009. 相似文献
18.
Kayed A. Abu Safieh Basem A. Moosa Mustafa M. El-Abadelah Salim S. Sabri Wolfgang Voelter 《Monatshefte für Chemie / Chemical Monthly》2008,139(2):147-151
Summary. 5-(Substituted) thieno[2′,3′:5,6]pyrido[3,4-b]indoles were synthesized via cyclocondensation of 3-(3-aminothien-2-yl)indole with the appropriate aldehyde in the presence of boron trifluoride etherate
under Pictet-Spengler reaction conditions. The constitution of the new compounds is evidenced from analytical and spectral (NMR and MS) data. 相似文献
19.
A. B. Serov V. G. Kartsev Yu. A. Aleksandrov F. M. Dolgushin 《Russian Chemical Bulletin》2005,54(10):2432-2436
A series of 6a′,7′,8′,9′-tetrahydrospiro[indoline-3,7′-pyrrolo[1,2-a]quinoline]-2-one derivatives were synthesized by the 1,3-dipolar cycloaddition reaction. The regio-and stereoselectivity
of the reaction were established by X-ray diffraction study.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2357–2361, October, 2005. 相似文献
20.
[reaction: see text] Reaction of 5,5-dimethyl-3-pyrazolidinone (1) with 2-indanone (2) gave 5,5-dimethyl-2-(1H-indenyl-2)-3-pyrazolidinone (3) instead of the expected azomethine imine 4. Although reaction of 2-substituted 3-pyrazolidinones with acetylenedicarboxylates usually gives ring expansion products, such as 1,2-diazepines, treatment of 3 with dialkyl acetylenedicarboxylates (5, R = Me; 6 R = Et) resulted in the formation of rel-(7aR,12aS)-6,7-bis(alkoxycarbonyl)-3,4-dihydro-4,4-dimethyl-7aH-indano[1,2-b]pyrrolo[1,2-a]pyrimidin-2-ones (7, R = Me; 9, R = Et) as major products and 3,4-bis(alkoxycarbonyl)-7,7-dimethyl-2-(indenyl-2)-6,7-dihydro-2H,6H-1,2-diazepin-5-ones (8, R = Me: 10, R = Et) as minor products. 相似文献