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1.
Benzylic zinc reagents add with high regioselectivity to 1-(phenoxycarbonyl) salts derived from pyridine-3-carboxaldehyde ( 1a ) or 3-acetylpyridine ( 1b ) to yield 1-(phenoxylcarbonyl)-4-benzyl-1,4-dihydropyridine-3-carboxaldehydes 5a, 5c or ketones 5b, 5d . Aromatizations of these dihydro analogues with sulfur led to the corresponding aldehydes 6a, 6c or ketones 6b, 6d . An alternate synthesis to the aldehydic precursors involved additions of benzylic zinc reagents to 1-(phenoxycarbonyl) salts formed from methyl nicotinates which led to the corresponding methyl 1-(phenoxycarbonyl)-4-benzyl-1,4-dihydronicotinates 7a, 7b . Aromatizations of 7a, 7b led to the corresponding pyridine esters 8a, 8b which on reduction with lithium aluminum hydride yielded the corresponding carbinols 9a, 9b . Oxidation of 9a, 9b by manganese dioxide afforded aldehydes 6e, 6f . Aldehydes 6a-f were readily converted into the benz[g]isoquinolines 10a-f on heating in polyphosphoric acid. 相似文献
2.
Resin-bound amines 1a-e condense with isothiocyanates to give thiourea resins 2a-i. Resins 2a-g subsequently react with iodomethane followed by cleavage affording S-methyl isothioureas 4a-g, and resins 2a-b,h-i react with acyl chlorides to afford N-acylated thioureas 6a-d. N-Acylthioureas 8a-f (R(2) = H) were prepared directly from resin-bound amines 1a-d with acyl isothiocyanates. N-Acylthioureas 8a-d,f(R(2) = H) were used for the preparation of S-methyl-N-acylisothioureas 10a-e. Alkylation was performed using methyl iodide. Resin-bound S-methyl-N-acylisothioureas 10a,b,d are converted by an action of hydrazines into 3-amino-1,2,4-triazoles 13a-d. Condensation of resins 8a-e (R(2) = H) with 2-bromoacetophenones in the presence of TEA affords thiazoles 15 a-e. All transformations proceeded in high yields and gave products of good purities. 相似文献
3.
Hydrolysis of ethyl 3-amino-4-aryl-cycloalka[e]thieno[2,3-b]pyridine-2-carboxylates ( 3a-d) gave the corresponding o-aminocarboxylic acids 4a-d . Heating the latter compounds ( 4a-d) with acetic anhydride furnished the oxazinone derivatives 5a-d which, in turn, underwent recyclization reaction to give the corresponding pyrimidinones 6a-d upon treatment with ammonium acetate in acetic acid. Reaction of 3-amino-4-aryl-cycloalka[e]thieno[2,3-b]pyridine-2-carboxamides ( 3f,h ) with triethyl orthoformate gave pyrimidinone derivatives 7a,b . Reaction of 3-amino-4-phenyl-cycloalka[e]thieno[2,3-b]pyridine-2-carboxamides 3e,h with aromatic aldehydes furnished tetrahydropyridothienopyrimidinones 8a-d . Chlorination of 7a,b and 6a-d by using phosphorous oxychloride produced 4-chlorocycloalka[5′,6′]pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine derivatives 9a-f which were used as key intermediates in the synthesis of several new cycloalkapyrido-thienopyrimidines 10a-f ˜ 14a-f . Moreover, some cycloalkapyridothienotriazinones 15a,b-17a,b were synthesized. 相似文献
4.
Lin YS Chang SY Yang MS Rao CP Peddinti RK Tsai YF Liao CC 《The Journal of organic chemistry》2004,69(2):447-458
The synthesis of 4-triflyloxy-2,6,6-trimethyl-2,4-cyclohexadienone (13), bicyclo[2.2.2]octenones 1a-j and 15a-j, and bicyclo[2.2.2]octadienones 2a-f, 6a-d, and 11a-f is described. The 2,4-cyclohexadienones 4 and 13 were used for the first time as nondimerizing and easily accessible alternatives to 2,6,6-trimethyl-2,4-cyclohexadienone 12 in Diels-Alder reactions with acetylene derivatives 5a-d to prepare the adducts 6a-d and 11a-e in excellent yields. Compounds 11a-d were initially prepared by the alcoholysis of 6a-d to afford bicyclo[2.2.2]octene-2,5-diones 7a-dfollowed by treatment of 7a-d with N-phenyltriflimide in the presence of LHMDS at -78 degrees C. Diels-Alder reaction of 13 with an acetylene equivalent, phenyl vinyl sulfoxide, was also studied. A detailed study of the Diels-Alder reactions of various olefinic dienophiles 14a-j with 13 has been carried out to furnish cycloadducts 15a-j in high yields. Reductive removal of triflyloxy group of vinyl triflates 11a-f and 15a-j was performed in the presence of [Pd(PPh(3))(2)Cl(2)-Bu(3)N-HCO(2)H] to obtain the desired bicyclo[2.2.2]octadienones 2a-f and bicyclo[2.2.2]octenones 1a-j, respectively, in good overall yields. 相似文献
5.
2-Amino-6-methylpyridine ( 4 ) reacts with active malonates 2a-d or 3a-d either in acetone solution with triethylamine as catalyst at room temperature or with active malonates 2a-d in acetone solution at reflux temperature to yield the pyrido[1,2-a]pyrimidines 5a-d . 2,6-Diaminopyridine ( 8 ) already reacts without triethylamine with 2a-d at room temperature to afford the pyrido[1,2-a]pyrimidines 9a-d . At higher temperatures pyrido[1,2-a]pyrimidines 5 and 9 are rearranged via ketene intermediates [1] to yield the 1,8-naphthyridines 6a-d , and 10a-d , respectively. The naphthyridines 6 and 10 can also be synthesized directly from 4 or 8 using either diethyl malonates 1 or — with better results — the active malonates 2 at 240–250°. Further reaction of 10a-e with 2c,d leads to the pyridonaphthyridines 12a-f . Nitration of 6c yields the nitro derivative 16 and chlorination of 6c,d gives 15c,d , while the chlorination of 10c affords the di-chloro derivative 17 . 相似文献
6.
H. M. Moustafa 《Phosphorus, sulfur, and silicon and the related elements》2013,188(7):1397-1412
2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (Lawesson's Reagent, LR, 1 ) reacts with cycloalkylidenecyanothioacetamides ( 2 and 3 ) to give 5'-cyano-2'-(4-methoxyphenyl)spiro [cyclopentane(cyclohexane)-1,6'-perhydro-[1,3,2]thiazaphosphixane]-2',4'-disulfide ( 4 and 5 ). The reaction of compounds 4 and 5 with f -halo compounds led to the formation of the substituted thio-compounds 6a-e and 7a-e , respectively, these compounds, upon treatment with sodium ethoxide, produce the corresponding thienothiazaphosphixine derivatives 8a-e and 9a-e respectively. Compounds 8a-e and 9a-e react with LR under different reaction conditions to give polyfused heterocyclic compounds 10a-d and 11a-d respectively. Treatment of compounds 8b and 9b with CS 2 and (CH 3 ) 2 SO 4 gave the corresponding dithiocarbamate methyl ester derivatives 12 and 13 , respectively, which on treating with hydrazine hydrate yielded compounds 14 and 15 respectively. Compounds 14 and 15 reacted with LR to yield compounds 16a , b and 17a , b respectively. 相似文献
7.
Synthesis and Characterization of New Heterocyclic Compounds Containing Thienylbenzo[h]Quinoline Moiety
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Elham A. Al‐Taifi Mohamed S. Abbady Etify A. Bakhite 《Journal of heterocyclic chemistry》2016,53(5):1479-1487
In this paper the reaction of 2‐(2′‐thienylmethylene)‐3,4‐dihydronaphthalen‐2(1H)‐one ( 1 ) with cyanothioacetamide gave a mixture of 3‐cyano‐5,6‐dihydro‐4‐(2′‐thienyl)‐benzo[h]quinolin‐2(1H)‐thione ( 2 ) and the related disulfide 3 . Compound 2 was reacted with some halo compounds namely; ethyl chloroacetate, chloroacetamide, chloro(N‐(p‐chlorophenyl))acetamide, N1‐chloroacetylsulfanilamide, and 2‐chloromethyl‐1H‐benzimidazole to produce a series of 2‐(substituted)methylthio‐3‐cyano‐5,6‐dihydro‐4‐(2′‐thienyl)benzo[h]quinolines 4a , 4b , 4c , 4d , 4e and 11 . Upon heating the latter compounds with sodium ethoxide, they underwent intramolecular Thorpe–Zeigler cyclization to furnish the corresponding 2‐(substituted)‐3‐amino‐5,6‐dihydro‐4‐(2′‐thienyl)‐benzo[h]thieno[2,3‐b]quinolines 5a , 5b , 5c , 5d , 5e and 12 . (3‐Cyano‐5,6‐dihydro‐4‐(2′‐thienyl)‐benzo[h]quinolin‐2‐ylthio)acethydrazide ( 8 ) and the related isomer, 3‐amino‐5,6‐dihydro‐4‐(2′‐thienyl)thieno[2,3‐b]benzo[h]quinoline‐2‐carbohydrazide ( 9 ), were also synthesized. Most of the aforementioned compounds were used as key intermediates for synthesizing other benzo[h]quinolines, benzo[h]thieno[2,3‐b]quinolines as well as benzo[h]pyrimido[4′,5′:4,5] thieno[2,3‐b]quinolines. The structure of all synthesized compounds was confirmed by spectroscopic measurements and analytical analyses. 相似文献
8.
Philip Yaw Boamah Norbert Haider Gottfried Heinisch Jran Moshuber 《Journal of heterocyclic chemistry》1988,25(3):879-883
8-Phenylpyrido[3,4-d]pyridazines bearing various amino substituents at C-5 ( 7a-d, 8 ) were prepared from ethyl 5-benzyl-4-pyridazinecarboxylate 1 via the fused pyridone 5 . The isomeric 4-phenylpyrido[2,3-d]pyridazines having the amino functions attached to C-2 ( 10a-f ) were obtained by a one-pot cyclization of the amino ketone 1 with appropriate acetamide acetals. These novel triazanaphthalene derivatives are of interest as analogues of diuretic and antithrombotic agents. 相似文献
9.
Yoshinori Tominaga Atsuyuki Ushirogochi Yoshiro Matsuda 《Journal of heterocyclic chemistry》1987,24(6):1557-1567
Reaction of aryl and styryl methyl ketones 1a-m with dimethyl bis(methylthio)methylenemalonate ( 2 ) in the presence of potassium hydroxide in dimethyl sulfoxide gave the corresponding methyl 6-aryl- and 6-styryl-4-methylthio-2-oxo-2H-pyran-3-carboxylates 3a-m . 6-Aryl derivatives 3a-d,g were treated with sodium methoxide in methanol to give the corresponding 6-aryl-4-methoxy-2H-pyran-2-ones 8a-d and 9. Phenylcoumalin ( 7a ) and paracotoin ( 7b ) were synthesized by the desulfurization of 6-aryl-4-methylthio-2H-pyran-2-ones 4a,b. Similarly, anibine ( 8e ) was also synthesized from 3g . Treatment of 3 with hydrogen peroxide or 3-chloroperoxybenzoic acid gave the corresponding 4-methylsulfiny-2H-pyran-2-ones 10a-f in good yields. Displacement reactions of 10a-f with nucleophilic reagents are also described. 相似文献
10.
Some novel Schiff bases have been prepared by reacting 6-azido-5-formyl-2-pyridone 1 with a series of aromatic amines 2a-f. 5-Arylaminomethylene-6-(E)-aryl-iminopyridones 3a-e were obtained by reaction of 1 with 2a-e at room temperature, whereas with 2f, the 6-azido-5-naphthalen-2-yl-iminomethylpyridone derivative 4 was formed. On the other hand, heating 1 with 2a-d at 140-150 degrees C yielded two sets of isomeric products, (E)-3a-d and (Z)-5a-d. Refluxing compounds (Z)-3a,c with hydroxyl-amine in methanol gave the corresponding hydroxyliminopyridones 8a,c. Heating of (E)-3a-d with excess POCl3 at reflux did not give the expected tricyclic compound 9, but rather the isomeric products (Z)-5a-d were obtained. The structures of all these products have been characterized using IR and 1H- and 13C-NMR spectroscopy. 相似文献
11.
Seiji Yamaguchi Kunihiro Tsuzuki Yoshie Sannomiya Yutaka Oh-Hira Yoshiyuki Kawase 《Journal of heterocyclic chemistry》1989,26(2):285-287
Some benzofuro[3,2-b]quinoline derivatives 1a-d and 3a were synthesized by condensation of 2-amino-benzaldehyde, 2-aminoacetophenone, 2-aminobenzophenone, isatin, or 2-aminobenzoic acid with 3(2H)-benzofuranone. The benzofuroquinolinone 3a was also obtained from 2-aminobenzoic acid and phenoxy-acetyl chloride in two steps and converted to 10-chloro derivative 1e . Similarly, some 8-halobenzofuro[3,2-b]-quinoline derivatives 1d,e and 3a (X = F, Cl, Br, I) were synthesized from 5-haloisatin or 2-amino-5-halo-benzoic acid. And benzofuro[3,2-b]quinolines 1a-e thus obtained were converted to corresponding N-oxides 2 . 相似文献
12.
Yoshifumi Watanabe Hirotaka Yoshiwara Munefumi Kanao 《Journal of heterocyclic chemistry》1993,30(2):445-451
The syntheses of 4-(benzo[b]furan-3-yl)piperidines, 4-(benzo[b]furan-2-yl)piperidines and 4-(benzo[b]thiophen-3-yl)piperidines with 5-HT2 antagonist activity are described. Reaction of 1-acetyl-4-(2,4-difluorobenzo-yl)piperidine 2 with methyl glycolate gave methyl 6-fluoro-3-(1-acetylpiperidin-4-yl)benzo[b]furan-2-carboxylate 3 , which was converted to 2-[2-[4-(benzo[b]furan-3-yi)piperidin-1-yl]ethyl-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]pyridin-3(2H)-one hydrochloride 9 . Analogous benzo[b]furans 17a-d and benzo[b]thiophenes 10a,b and 18a were prepared by a similar method. Cyclization of 4-fluoro-2-(4-pyridinylmethoxy)acetophenones 20a,b afforded 4-(benzo[b]furan-2-yl)pyridines 21a,b , which were converted to 2-[2-[4-(benzo[b]furan-2-yl)-piperidin-1-yl]ethyl-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one hydrochlorides 24a,b. Among them, benzo[b]furans 9 and 17a,d and benzo[b]thiophenes 10 and 18a showed potent 5-HT2 antagonist activity in vitro. 相似文献
13.
Prabha Kolandaivel Satheeshkumar Rajendran Rajendra Prasad Karnam Jayarampillai 《Journal of heterocyclic chemistry》2021,58(9):1809-1824
A schematic study on the condensation of 2,4-dichloroquinolines ( 1 ) with 1-naphthyamine ( 2 ) in the presence of CuI as a catalyst to functionalized mono ( 3 ) and di ( 4 ) substituted naphthylamino quinolines was described. Consequently, these mono- and di-substituted amines on polyphosphoric acid-catalyzed cyclization reaction with p-toluic acid and acetic acid to yield the linear benzo[b]naphtho[2,1-g][1,8]naphthyridines ( 5 ) and angular benzo[b]naphtho[2,1-h] naphthyridines ( 6 ) in good yields. In addition to descried the similar synthesis of benzo[g]naphtho [2,1-b][1,8]naphthyridines ( 12 ) and benzo[h]naphtho[2,1-g][1,8]naphthyridines ( 13 ) from 2,4-dichlorobenzo[h]quinoline ( 8 ) with various anilines ( 9 ) through my intermediates ( 10 and 11 ). 相似文献
14.
Essam Mohamed Sharshira Haruki Iwanami Mutsuo Okamura Eietsu Hasegawa Takaaki Horaguchi 《Journal of heterocyclic chemistry》1996,33(1):17-25
Photocyclization reactions were carried out on 8-alkoxy-1,2,3,4-tetrahydro-1-naphthalenones (six-membered ring ketones) 4a-g and 4-alkoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ones (seven-membered ring ketones) 5a -e in acetonitrile. Irradiation of 4a-f gave rearranged naphthyl alcohols 8a-f as major products. In the case of 4g , 2a,3,4,5-tetrahydronaphtho[1,8-bc]furan-2a-ol 6g was obtained. In contrast, irradiation of 5a-e afforded 2,2a,3,4,5,6-hexahydrocyclohepta[cd]benzofuran-2a-ols 9a-e in good yields. The difference in reactivities between 4a-g and 5a-e is attributed to the conformation of six- and seven-membered rings. Conformational and substituent effects in cyclization step of 1,5-biradicals are discussed along with reaction pathways. 相似文献
15.
A new, convergent synthesis of hexahomotriazacalix[3]arenes 1a-e is described. The key transformation in this synthesis involves the coupling of the triamines 4a-d with 2, 6-bis(chloromethyl)-4-methylphenol 5 and results in the formation of the hexahomotriazacalix[3]arenes 1a-d in 90-95% yield. The triamines 4a-d were constructed by the one-pot reaction of monochloroaldehyde 3 and a primary amine followed by reduction to yield the triamines 4a-d in 50-55% yield. Deallylation of macrocycle 1d was accomplished by palladium catalysis to obtain the N-unsubstituted macrocycle 1e, which has the potential to be a precursor to a variety of N-substituted hexahomotriazacalix[3]arenes. 相似文献
16.
Thomas Zimmermann 《Journal of heterocyclic chemistry》2000,37(4):885-889
The diastereoselective synthesis of 6‐aroyl‐3,5‐diarylspiro[cyclohexa‐2,4‐diene‐1,2′2′,3′‐dihydro‐1′H‐benzo[e]indoles] 6 and ‐benzo[g]indoles] 7 from 2,4,6‐triarylpyrylium perchlorates 1 and in situ generated 2‐methylene‐2,3‐dihydro‐1H‐benzo[e]indoles 3 or ‐benzo[g]indoles 5 (anhydrobases of the corresponding 2‐methyl‐1H‐benzo[e]indolium perchlorates 2 and 2‐methyl‐3H‐benzo[g]indolium perchlorates 4 , respectively) in the presence of triethylamine/acetic acid in ethanol by a 2,5‐[C4+C2] pyrylium ring transformation is reported. Spectroscopic data of the transformation products and their mode of formation are discussed. 相似文献
17.
Demetrios N. Nicolaides R. Wajih Awad Evangelia A. Varella 《Journal of heterocyclic chemistry》1996,33(3):633-637
10-(Methoxyimino)phenanthrene-9-one 1 reacts thermally with the arylacetic derivatives 2(a-j ) to yield the corresponding 1,4-benzoxazin-2-ones 4(a-d,f ) and benzo[d]oxazoles 5(a-e,g ). Similarly, reaction of the monoximes 7a, 7b with compounds 2a, 2d respectively affords 8a, 8b , while action of trans-stilbene on the monoximes 1, 7a, 7b leads to the 1,4-benzoxazines 10, 11, 13 , obtained along with the corresponding 2-phenyloxazoles 5a, 8a, 8c and compound 12 . 相似文献
18.
The coupling of dimethyl acetonedicarboxylate 1 with a variety of aryldiazonium salts 2a-i produces the hydrazones 3a-i which can be cyclized in boiling dichlorobenzene to yield the pyridazone esters 4a-i , or in sodium hydroxide solution to give the pyridazone acids 5a-f,h,i , which can be decarboxylated at elevated temperatures. The hydroxy group in 4a,d can be acylated, sulfonated or alkylated yielding compounds 8a-n . Condensation of 4a,d with magic malonates 9a-d produces the pyronopyridazinones 10a-f . The reaction of 4a with hydrazine yields the hydrazide 12 via the salt 11 , and with ammonia the amide 14 . 相似文献
19.
Yoshinori Tominaga Yoshihide Shiroshita Tomohiko Kurokawa Hiromi Gotou Yoshiro Matsuda Akira Hosomi 《Journal of heterocyclic chemistry》1989,26(2):477-487
The reaction of 1-ethoxycarbonylmethylpyridinium bromides 5a-k with nitro ketene dithioacetal, 1,1-bis-(methylthio)-2-nitroethylene ( 2 ), in the presence of triethylamine in ethanol gave the desired ethyl 2-methyl-thioindolizine-3-carboxylates 3a-k in good yields, along with ethyl 2-methylthio-1-nitroindolizine-3-carboxyl-ates 4a-d . Deesterification of 3 using sodium hydroxide in methanol followed by treatment with polyphosphoric acid gave the corresponding 2-methylthioindolizines 5a-d in good yields. The desulfurization of 5 with Raney-nickel in ethanol occurs smoothly to give the 1,2,3-unsubstituted indolizines 6a-c (a , parent indolizine; b , 8-methylindolzine; c , 6,8-dimethylindolizine). Similarly, pyrrolo[2,1-a]isoquinoline ( 19 ) was also synthesized. These indolizine and pyrrolo[1,2-a]isoquinoline derivatives were allowed to react with dimethyl acetylene to give the corresponding cycl[3.2.2]azine and benzo[g]cycl[3.2.2]azine derivatives in good results. 相似文献
20.
N. G. Kozlov L. S. Yakubovich V. L. Murashko 《Russian Journal of Electrochemistry》2000,36(6):777-780
The condensation of ethyl cyclopentanone-2-carboxylate withN-arylmethylene-2-naphthylamines depending on the conditions of reaction affords 4-aryl-l-ethoxycarbonyl-lH-2,3,4,5-tetrahydrocyclopenta-[c]benzo[f]quinolines, 4-aryl-l-ethoxycarbonyl-lH-2,3-dihydrocyclopenta[c]benzo[f]quinolines, and 4-aryllH-2,3-dihydrocyclopenta[c]benzo[f]quinolines. 相似文献