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1.
Azaindole derivatives. 67. Synthesis of N-substituted 1-benzyl-4-methyl-5-cyano-6-amino-7-azaindoles
N-substituted 1-benzyl-4-methyl-5-cyano-6-amino-7-azaindoles have been synthesized from the respective 1-benzyl-4-methyl-5-cyano-6-chloro(and 6-hydroxy)-7-azaindoles. The effect of the 5-cyano group on the oxidation-reduction processes accompanying nucleophilic replacement of chlorine in 6-chloro-7-azaindoles by primary and secondary amines has been considered. 7-Azaindoline compounds were dehydrogenated by chloranil to N-substituted 1-benzyl-4-methyl-5-cyano-6-amino-7-azaindoles.For communication 66, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 91–96, January, 1986. 相似文献
2.
A general and efficient procedure for the synthesis of 2,3-disubstituted 5-azaindoles through the palladium-catalyzed heteroannulation of 4-acetamido-3-iodopyridines and diaryl-, dialkyl-, or arylalkylalkynes is described along with a study of the reaction regioselectivity. The preparation of 2-monosubstituted 5-azaindoles via sila-Sonogashira/5-endo cyclization is also reported. These methods allowed us to prepare 36 diversely substituted 5-azaindoles in good yields. 相似文献
3.
Pictet-Spengler condensation of 2-(aryl)-2-(1H-pyrrol-2-yl)ethanamines using conventional acid catalysts like TMSCl or TFA resulted in the formation of substituted 5-azaindoles involving a tandem one pot four steps reaction sequence. By contrast use of glacial acetic acid furnished the targeted tetrahydro-5-azaindoles in diastereoselective manner. These were readily dehydrogenated to 5-azaindoles. 相似文献
4.
《Tetrahedron letters》1998,39(29):5159-5162
In an effort to develop synthetic procedures for the preparation of 2-substituted 5-azaindoles, the synthesis and cyclization reactions of acetylenic aminopyridines was explored. A novel method for the synthesis of 2-substituted 5-azaindoles via a transition metal catalyzed reaction is described. 相似文献
5.
Michael N. Balfour Julio Zukerman-Schpector Maria José Dávila Rodriguez Joel Savi Reis Carlos Henrique A. Esteves 《合成通讯》2019,49(3):351-358
The synthesis of a library of 2,6-disubstituted-azaindoles relying on Sonogashira cross-coupling and intramolecular cyclization is described. Eleven examples of 6-alkynyl derivatives and three examples of 3-bromo-5-azaindoles are reported. One of the 3-bromo-5-azaindoles was also further functionalized with two different aryl trifluoroborate salts via Suzuki-Miyaura coupling reaction. 相似文献
6.
Nabih S. Girgis Steven B. Larson Roland K. Robins Howard B. Cottam 《Journal of heterocyclic chemistry》1989,26(2):317-325
Certain 4-substituted 1H-pyrrolo[2,3-b]pyridines (7-azaindoles) undergo a nucleophilic substitution-rearrangement upon treatment with various primary amines at elevated temperatures to yield N-1-substituted 4-amino-1H-pyrrolo[3,2-c]pyridines (5-azaindoles). Treatment of the same 7-azaindoles with secondary amines under the same reaction conditions led to simple nucleophilic substitution products. 相似文献
7.
T. V. Sycheva N. M. Rubtsov Yu. N. Sheinker L. N. Yakhontov 《Chemistry of Heterocyclic Compounds》1987,23(1):82-87
Electrophilic substitution in the 3-position of 1-benzyl-4-methyl-5-cyano-6-chloro-7-azaindole requires more severe conditions than in 7-azaindoles without the 5-cyano-substituent. Increased ease of nucleophilic replacement of the chlorine atom by the methoxy group has been observed in 1-benzyl- (and 1-butyl)-4-methyl-5-cyano-6-chloro-7-azaindoles, and the cyano-group in these compounds has been found to be resistant to hydrolysis and alcoholysis. The introduction into 1-benzyl- (and 1-butyl)-4-methyl-6-hydroxy-7-azaindoles of a 5-cyano-substituent results in a shift of the lactam-lactim tautomeric equilibrium towards the lactim forms.For communication 68, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 100–106, January, 1987. 相似文献
8.
Electrophilic substitution reactions — cyanomethylation, bromination, nitration, and the Mannich reaction- in the 5-azaindole series were studied. It is shown that, despite the literature data, 5-azaindole behaves like the isomeric 4- and 7-azaindoles in these reactions. Conditions that make it possible to synthesize various 3-substituted 5-azaindoles in high yields were found.See [1] for communication XL.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1528–1530, November, 1972. 相似文献
9.
John J. Caldwell 《Tetrahedron letters》2007,48(9):1527-1529
Nucleophilic aromatic substitution of 4-chloro- and 4-fluoro-7-azaindoles with cyclic secondary amines under microwave heating gave a straightforward and rapid synthesis of 4-(cyclic dialkylamino)-7-azaindoles. 4-Fluoro-7-azaindoles showed a greater reactivity towards SNAr reactions under these conditions than 4-chloro-7-azaindole. 相似文献
10.
Rina Chun Saegun Kim Sang Hoon Han Ashok Kumar Pandey Neeraj Kumar Mishra In Su Kim 《Tetrahedron letters》2018,59(43):3848-3852
The site-selective C–H nitration reaction of 7-azaindoles with t-butyl nitrite under palladium catalysis is described. This protocol provides an efficient method for the construction of ortho-nitrated N-aryl-7-azaindoles with excellent site-selectivity and functional group compatibility. The formed 7-azaindole derivatives can be readily transformed into 7-azaindoles containing an aniline functional group under palladium-catalyzed hydrogenation conditions. 相似文献
11.
Electrophilic substitution reactions (cyanomethylation, bromination, nitration, Mannich reaction) are investigated in some 4-azaindoles. The effect on reactivity of the presence of an acyl group in the 1-position is examined. Conditions have been found for the synthesis in high yield of various 3-substituted 4-azaindoles.For part XXX, see [1]. 相似文献
12.
Chang Sung Hong 《Tetrahedron letters》2007,48(28):4831-4833
N-Arylation of 5- and 7-azaindoles was achieved in LiCl-mediated catalytic CuI reactions at 120 °C with moderate to high yields. N-Arylation can be performed with various arylhalides, such as phenyl, pyridine, quinoline, thiophen, and thiazole moieties. 相似文献
13.
L. N. Yakhontov M. Ya. Uritskaya M. V. Rubtsov 《Chemistry of Heterocyclic Compounds》1966,1(6):625-630
A new method for synthesizing 5- and 7-azaindoles is given, -Chlorobutyronitrile and malonyl chloride give 2, 4, 6-trichloro-3-(ß-chloroethyl) pyridine, which is cyclized with ammonia to 4, 6-dichloro-7-azaindoline and 4, 6-dichloro-5-azaindoline. 6-Chloro derivatives of 7-azaindolines are not dehydrogenated by chlorainil, but 2, 3-dichloro-S, 6-dicyanobenzoquinone converts them to 6-chloro-7-azaindoles. It is shown that sodium in liquid ammonia is an effective means of dehydrogenating the 5-azaindoline to 5-azaindole. In this case, dehydrogenation of 4, 6-dichloro-7-azaindoline is followed by dehalogenation.For Part IX see [1]. 相似文献
14.
3-(Hetero)aryl substituted indoles, 7-azaindoles, and pyrroles can be obtained in a very concise fashion via a one-pot Masuda borylation-Suzuki coupling sequence. The concise total syntheses of the marine natural products meridianins A (5) and G (4i) nicely illustrate the utility of this methodology. 相似文献
15.
1-Hydroxy derivatives of 2,3-disubstituted 6-azaindoles, which were converted to the corresponding 2,3-disubstituted 6-azaindoles, were obtained from the products of condensation of 3-nitro-4-chloropyridine with acetoacetic and benzoylacetic esters and acetylacetone.See [1] for communication LIII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 492–495, April, 1978. 相似文献
16.
Zhang Z Yang Z Wong H Zhu J Meanwell NA Kadow JF Wang T 《The Journal of organic chemistry》2002,67(17):6226-6227
Conditions for attachment of acetyl chloride, benzoyl chloride, and chloromethyl oxalate to the 3-position of 4-, 5-, 6-, or 7-azaindoles were explored. Best results were achieved with an excess of AlCl(3) in CH(2)Cl(2) followed by the addition of an acyl chloride at room temperature. 相似文献
17.
Mohamed Yacine Ameur Messaoud Ghenia Bentabed-Ababsa Ziad Fajloun Monzer Hamze Yury S. Halauko Oleg A. Ivashkevich Vadim E. Matulis Thierry Roisnel Vincent Dorcet Florence Mongin 《Molecules (Basel, Switzerland)》2021,26(20)
Five protocols were first compared for the copper-catalyzed C-N bond formation between 7-azaindole and aryl/heteroaryl iodides/bromides. The 1-arylated 7-azaindoles thus obtained were subjected to deprotometalation-iodolysis sequences using lithium 2,2,6,6-tetramethylpiperidide as the base and the corresponding zinc diamide as an in situ trap. The reactivity of the substrate was discussed in light of the calculated atomic charges and the pKa values. The behavior of the 1-arylated 7-azaindoles in direct iodination was then studied, and the results explained by considering the HOMO orbital coefficients and the atomic charges. Finally, some of the iodides generated, generally original, were involved in the N-arylation of indole. While crystallographic data were collected for fifteen of the synthesized compounds, biological properties (antimicrobial, antifungal and antioxidant activity) were evaluated for others. 相似文献
18.
Lourdes Rodriguez-Salvador Elena Zaballos-Garcia Eugenia Gonzalez-Rosende Mohamed Djebouri Sidi José Sepúlveda-Arques R. Alan Jones 《合成通讯》2013,43(8):1439-1447
2-Vinyl-4-azaindoles are less reactive with dienophiles than 2-vinylindoles. 5-Methoxy-2-vinyl-4-azaindole 2a and its 1-methyl derivative 2a reacts with N-phenylmaleimide to yield cycloadducts only under vigorous conditions. 2b produces a cycloadduct with dimethyl acetylenedicarboxylate, while 2a yields a Michael-type adduct. Reactions with more reactive dienophiles gave only polymeric products. 相似文献
19.
A one-pot synthesis of a variety of substituted 4-, 6-, and 7-azaindoles from commercially available aminopyridines in moderate to good yields is described. 相似文献
20.
Song JJ Tan Z Gallou F Xu J Yee NK Senanayake CH 《The Journal of organic chemistry》2005,70(16):6512-6514
Dilithiation of 3-amino-4-picoline (1) was achieved with sec-BuLi at room temperature. Condensation of the resulting dianion (2) with carboxylic esters afforded a wide range of 2-substituted 6-azaindoles in good yields. 相似文献