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1.
Deepak Kumar Barange 《Tetrahedron》2007,63(8):1775-1789
We describe a practical and elegant method of constructing a thiazine ring fused with benzene under mild reaction conditions. A variety of 4-iodo-2H-benzo[e][1,2]thiazine-1,1-dioxides were prepared with high regioselectivity via a two-step process involving Pd/C-mediated C-C coupling of o-halobenzenesulfonamides with terminal alkynes, followed by iodocyclization of the resulting o-(1-alkynyl)arenesulfonamide using elemental iodine in acetonitrile. The coupling reaction was carried out using 10% Pd/C-PPh3-CuI as a catalyst system in the presence of Et3N. The process worked well for bromides and iodides, and a wide array of terminal alkynes containing alkyl and aryl substituents were employed. The iodocyclization step tolerated a variety of functional groups such as hydroxy, chloro, cyano, and methoxy, producing the six-membered heterocyclic ring selectively. The resulting 4-iodo-2H-benzo[e][1,2]thiazine-1,1-dioxides participated in Sonogashira, Heck, and Suzuki reactions producing a wide range of functionally substituted benzothiazines in good yields. 相似文献
2.
Diethyl ethoxymethylenemalonate was used for the novel synthesis of the triheterocyclic 3-carbethoxy-9,ll-disubstituted-4-oxo-4H-pyrido[3,2-e]pyrimido[1,2-c]pyrimidines from 4-aminopyrido[2,3-d]pyrim-idines via thermal cyclization of the intermediate ethyl 2-carbethoxy-3-[5,7-disubstituted-4-amino-pyrido[2,3-d]pyrimidin-4-yl]acrylates. The alkaline hydrolysis of 3-carbethoxy-4-oxo-4H-pyrido[3,2-e]-pyrimido[1,2-c]pyrimidines was performed to give corresponding acid derivatives. 相似文献
3.
The reaction of methyl 2-bromo-6-(trifluoromethyl)-3-pyridinecarboxylate ( 1 ) with methanesulfonamide gave methyl 2-[(methylsulfonyl)amino]-6-(trifluoromethyl)-3-pyridine-carboxylate ( 2 ). Alkylation of compound 2 with methyl iodide followed by cyclization of the resulting methyl 2-[methyl(methylsulfonyl)amino]-6-(trifluoromethyl)-3-pyridinecarboxylate ( 3 ) yielded 1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide ( 4 ). The reaction of compound 4 with α,2,4-trichlorotoluene, methyl bromopropionate, methyl iodide, 3-trifluoromethylphenyl isocyanate, phenyl isocyanate and 2,4-dichloro-5-(2-propynyloxy)phenyl isothiocyanate gave, respectively, 4-[(2,4-dichlorophenyl)methoxy]-1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazine 2,2-dioxide ( 5 ), methyl 2-[[1-methyl-2,2-dioxido-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4-yl]oxy]propanoate ( 6 ), 1,3,3-trimethyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide ( 7 ), 4-hydroxy-1-methyl-7-(trifluoromethyl)-N-[3-(trifluoromethyl)phenyl]-1H-pyrido[2,3-c][1,2]thiazine-3-carboxamide 2,2-dioxide ( 8 ), 4-hydroxy-1-methyl-7-(trifluoromethyl)-N-phenyl-1H-pyrido[2,3-c][1,2]thiazine-3-carboxamide 2,2-dioxide ( 9 ) and N-[2,4-dichloro-5-(2-propynyloxy)phenyl]-4-hydroxy-1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2] thiazine-3-carboxamide 2,2-dioxide ( 10 ). 相似文献
4.
M. Robba M. Cugnon de Sevricourt J. M. Lecomte 《Journal of heterocyclic chemistry》1975,12(3):525-527
The cyclization reactions of the 4-hydrazinothieno[2,3-d]pyrimidines give s-triazolo[1,2-c]-thieno[3,2-e]pyrimidines and tetrazolo[1,5-c]thieno[3,2-e]pyrimidines. 相似文献
5.
Krayushkin M. M. Yarovenko V. N. Semenov S. L. Zavarzin I. V. Martynkin A. Yu. Uzhinov B. M. 《Russian Journal of Organic Chemistry》2003,39(11):1656-1659
Reductive cyclization by McMurry method was performed with diketosulfide obtained by treating with Na2S of compound prepared by regioselective acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate with chloroacetyl chloride. As a result was synthesized a photochromic 1,2-dihetarylethene where the fuzed rings are connected by a 2,5-dihydrothiophene ring. The oxidation of the latter provides 2,5-dihydrothiophene-1,1-dioxide bridge. 相似文献
6.
N. A. Larionova A. A. Zubarev L. A. Rodinovskaya A. M. Shestopalov 《Russian Chemical Bulletin》2013,62(5):1304-1306
A new highly selective method was developed for the synthesis of substituted thieno[3,2-b]-pyridines based on the domino reaction of monopotassium salt (rather than dipotassium one) of carbamoylcyanodithioacetic acid with ethyl 4-chloroacetoacetate. Substituted 5H-pyrano[2,3-d]-thieno[3,2-b]pyridines were synthesized based on these thieno[3,2-b]pyridines. 相似文献
7.
M. M. Krayushkin I. P. Sedishev V. N. Yarovenko I. V. Zavarzin L. G. Vorontsova Z. A. Starikova B. V. Nabatov 《Russian Journal of Organic Chemistry》2005,41(9):1349-1353
A procedure was proposed for regioselective acylation of methyl 2-methyl-4H-thieno[3,2-b]-pyrrole-5-carboxylate with 2-(3-indolyl)-2-oxoacetyl chloride. Reactions of the resulting methyl 6-[2-(3-indolyl)-1,2-dioxoethyl]-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate with aromatic aldehydes and ammonium acetate in acetic acid afforded the corresponding methyl 6-[2-aryl-4-(3-indolyl)imidazol-5-yl]-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylates. The structure of methyl 6-[2-(4-chlorophenyl)-4-(3-indolyl)imidazol-5-yl]-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate was studied by X-ray analysis. 相似文献
8.
A synthesis of 4-N-oxides and of 3-hydroxy derivatives of 1,3-dihydro-2H-benzofuro[3,2-e][1,4]diazepin-2-ones and of 2,3-dihydro-1H-benzofuro[3,2-e][1,4]diazepines is described. Condensation of 2-acetyl- and 2-benzoyl-3-ethoxycarbonylaminobenzofurans with acrylonitrile gave derivatives of 1,2-dihydro- and of 1,2,3,4-tetrahydrobenzofuro[3,2-b]pyridine. 相似文献
9.
Some new 7,9-disubstituted 7H-1,2,3,4-tetrazolo[1,5-c]pyrrolo[3,2-e]pyrimidines 5 have been synthesized either by diazotization of 4-hydrazino-5,7-disubstituted-7H-pyrrolo[2,3-d]pyrimidines 4 obtained by hydrazinolysis of 4-chloro-5,7-disubstituted-7H-pyrrolo[2,3-d]pyrimidines 3 or via a substitution reaction between 3 and sodium azide. 5,7-Disubstituted-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-ones 2 were obtained by cyclocondensation of 2-amino-3-cyano-1,4-disubstituted pyrroles 1 with formic acid which on chlorination using phosphorus oxychloride afforded 3 . A novel route for the synthesis of 4-amino-5,7-disubstituted-7H-pyrrolo[2,3-d]pyrimidines 6 by the reductive ring cleavage of 5 has been reported. 相似文献
10.
N. V. Bubnov E. S. Denislamova P. S. Silaichev P. A. Slepukhin A. N. Maslivets 《Russian Journal of Organic Chemistry》2012,48(5):694-698
1-Aryl-4-aroyl-5-methoxycarbonyl-1H-pyrrole-2,3-diones react with 3-arylamino-1H-inden-1-ones affording 1,1??-diaryl-3??-aroyl-4??-hydroxy-1H-spiro[indeno[1,2-b]pyrrole-3,2??-pyrrole]-2,4,5??(1??H)-triones. The crystal and molecular structure of 4??-hydroxy-3??-(2,4-dimethylbenzoyl)-1,1??-diphenyl-1H-spiro[indeno[1,2-b] pyrrole-3,2??-pyrrole]-2,4,5??(1??H)-trione. 相似文献
11.
The reaction of 2-chloro-4-(methylsulfonyl)benzoyl chloride ( 5 ) with 1-methyl-1H-2,1-benzothiazin-4-(3H)-one 2,2-dioxide ( 4 ) gave the O-benzoyl compound, 1-methyl-2,2-dioxido-1H-2,1-benzothiazin-4-yl 2-chloro-4-(methylsulfonyl)benzoate ( 6 ), which rearranged to give the C-benzoyl isomer, [2-chloro-4-(methylsulfonyl)phenyl] (4-hydroxy-1-mefhyl-2,2-dioxido-1H-2,1-benzothiazin-3-yl)methanone ( 7 ). The O-cinnamoyl compound 13 that resulted from the addition of 2,4-dichlorocinnamoyl chloride ( 11 ) to compound 4 rearranged to give the C-cinnamoyl compound, 3-(2,4-dichlorophenyl)-1-(4-hydroxy-1-methyl-2,2-dioxido-1H-2,1-benzothiazin-3yl)-2-propen-1-one ( 15 ). On the other hand, 1-methyl-2,2-dioxido-1H-2,1-benzothiazin-4-yl 3-phenyl-2-propenoate ( 19 ) (from cinnamoyl chloride ( 17 ) and compound 4 ) rearranged to give 2,3-dihydro-6-methyl-2-phenyl-4H,6H-pyrano[3,2-c][2,1]benzothiazin-4-one 5,5-dioxide ( 21 ), an example of a hitherto unknown ring system. Additional examples of this novel heterocycle were prepared from 1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide ( 23 ) and 1-methyl-1H-thieno[3,2-c][1,2]thiazin-4(3H)-one 2,2-dioxide ( 8 ). 相似文献
12.
Synthetic approaches towards new condensed thienopyridine ring systems including furo[2,3-b]thieno[3,2-e]pyridines, bisthieno[2,3-b:3′,2′-e]pyridines, 5H-chromeno[2,3-b]thieno[3,2-e]pyridines, 5H-benzo(f)chromeno[2,3-b]thieno[3,2-e]pyridines have been achieved by application of intramolecular 4+2 cycloaddition reactions of suitably designed thieno[2,3-e][1,2,4]triazines tethered with alkene or alkyne terminals. 相似文献
13.
Alkoxide-promoted ring expansion of the novel ethyl 2-(6,7-dimethoxy-3-oxo-3,4-dihydrobenzo[e][1,2]thiazine-1,1-dioxide-2-yl)acetate 3a and analogous 4,4-diethyl derivative 3b and cyclization of methyl 2-[2-(phenylaminocarbonylmethyl sulfamoyl)-4,5-dimethoxyphenyl] acetate 9 to the corresponding new 3-carboxylates and 3-carboxanilide of 7,8-dimethoxy-4-hydroxy-2,5-dihydrobenzo[f][1,2]thiazepine-1,1-dioxide (5a,b and 10 respectively) is described. Compound 5a was deacylated upon treatment with sodium hydroxide followed by hydrochloric acid to give 7,8-dimethoxy-2,3-dihydrobenzo[f][1,2]thiazepine-1,1-dioxide-4 (5H)-one 8 and its N-ethyl derivative transferred to 6,7-dimethoxy-2-ethyl-3-oxo-3,4-dihydrobenzo[e][1,2]thiazine-1,1-dioxide 7 by the reaction with ethyl methyl ketone in the presence of pyrrolidine. 相似文献
14.
Abdelali Daich Frantisek Povazanec Bernard Decroix 《Journal of heterocyclic chemistry》1991,28(8):1911-1915
The appropriate substituted carbonylazides I treated with warm acetic acid give the corresponding acetamide IV or the cyclic lactam VI . This is a convenient route to 10,11-Dihydro-5H-pyrrolo[1,2-a][1,4]-benzodiazepin-11-one and 10,11-Dihydro-4H-thieno[2,3-e]pyrrolo[1,2-a][1,4]diazepin-10-one. 相似文献
15.
G. A. Gazieva N. G. Kolotyrkina A. N. Kravchenko N. N. Makhova 《Russian Chemical Bulletin》2014,63(2):431-434
Diastereoselective [3+2] cycloaddition of azomethine ylide to 1,3-dimethyl-6-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)-3a,9a-diphenyl-3,3a,9,9a-tetrahydroimidazo[4,5-e]thiazolo[3,2-b]-[1,2,4]triazine-2,7(1H,6H)-dione yields hitherto unknown 1,1′,3-trimethyl-3a,9a-diphenyl-3,3a,9,9a-tetrahydrodispiro(imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazine-6,3′-pyrrolidine-4′,3″-indole)-2,2″,7(1H,1″H)-triones. 相似文献
16.
A new and efficient method for the synthesis of hitherto unreported spiro[benzo[4,5]thiazolo[3,2-a]chromeno[2,3-d]pyrimidine-14,3′-indoline]-1,2′,13(2H)-triones was developed via the Domino Knoevenagel condensation–Michael addition–intermolecular cyclization sequences of isatin derivatives, cyclohexane-1,3-diones, and 2-hydroxy-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-ones, employing 12-tungstophosphoric acid (H3PW12O40) as an effective and inexpensive catalyst. 相似文献
17.
Condensation of 1,2-indanedione and 1,2,3-indanetrione hydrate (ninhydrin) with 2,3-diamino-pyridines gave a number of compounds belonging to the hitherto unknown 6H-indeno[1,2-b]-pyrido[3,2-e]pyrazine ring system. The unsymmetrical nature of the reactants can theoretically result in isomeric ring closure products. Assignment of the 6H- ring system was based upon the identity of 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one obtained from 2,3-diaminopyridine and ninhydrin with material prepared by unequivocal synthesis. The direction of cyclization of ninhydrin and 1,2-indanedione with the diamines was shown to be the same by reduction of the indenopyridopyrazinones to the corresponding indenopyridopyrazines. Some physical, chemical, and tumor growth-inhibitory properties of the products are reported. 相似文献
18.
Massimo Pregnolato Pietro Borgna Marco Terreni 《Journal of heterocyclic chemistry》1995,32(3):847-850
A convenient synthesis of 3H-thieno[3,2-c]-1,2-dithiole-3-thione (7) is proposed. The reaction of 7 with n-butylamine afforded the N-butylthieno[3,2-c]isothiazole-3(2H)-thione (7a) in dynamically equilibrium [1] with its 3H-thieno[3,2-c]-1,2-dithiole-N-butyl-3-imino isomer 7b. Characterizations and antimicrobial activities of the synthesized products are reported. 相似文献
19.
V. V. Dabaeva A. S. Noravyan V. N. Madakyan B. D. Enokyan 《Chemistry of Heterocyclic Compounds》1997,33(6):741-744
Two different convenient methods have been developed for the synthesis of condensed thieno[2,3-b]pyridines. The intramolecular cyclization of 3-amino-2-hydrazinocarbonyl-7,7-dimethyl-7,8-dihydo-5H-pyrano[3,4-e]-thieno[2,3-b]pyridine was carried out to give 7,7-dimethyl-2-oxo-1,2,6,7-tetrahydro-9H-pyrano[3′,4′-e]-imidazo[4″,5″∶2,3]thieno[5,4-b]pyridine, which is the first representative of a new heterocyclic system. 相似文献
20.
Umberto M. BattistiMarina M. Carrozzo Giuseppe Cannazza Daniela BraghiroliCarlo Parenti Livio BrasiliCinzia Citti Luigino Troisi 《Tetrahedron letters》2012,53(9):1122-1125
A new efficient and versatile synthesis to obtain different substituted 5,6-dihydro-8H-[1,2,4]thiadiazino[6,5,4-de]phenanthridine 4,4-dioxide and 5,6-dihydro-8H-[1,2,4]-thiadiazino[6,5,4-ij]thieno[2,3-c]quinolone 4,4-dioxide was developed. The four cyclic systems are achieved by a three-step synthesis proceeding under mild conditions in high yields. 相似文献