共查询到20条相似文献,搜索用时 15 毫秒
1.
Ding M He F Poss MA Rigat KL Wang YK Roberts SB Qiu D Fridell RA Gao M Gentles RG 《Organic & biomolecular chemistry》2011,9(19):6654-6662
Three synthetic approaches have been developed that allow efficient access to novel heteroaryl fused indole ring systems, including: 7,8,9,10-tetrahydro-6H-azepino[1,2-a]indoles, 4-oxo-2,3-dihydro-1H-[1,4]diazepino[1,7-a]indoles and 1,2,4,5-tetrahydro-[1,4]oxazepino[4,5-a]indoles. Each strategy is fully exemplified and the relative merits and limitations of the approaches are discussed. The hepatitis C virus (HCV) non-structural 5B (NS5B) polymerase inhibitory activities of select examples from each molecular class are briefly presented. 相似文献
2.
Katritzky AR Tymoshenko DO Monteux D Vvedensky V Nikonov G Cooper CB Deshpande M 《The Journal of organic chemistry》2000,65(23):8059-8062
The novel three-carbon synthon 1-(1H-1,2, 3-benzotriazol-1-yl)-3-chloroacetone for the synthesis of benzothiazoles, pyrido[1,2-a]indoles, and styryl-substituted indolizines and imidazo[1,2-a]pyridines is reported. The proposed routes are a general and efficient approach for heterocyclizations followed by benzannelations or attachment of arylethenyl pharmacophores. 相似文献
3.
A simple and efficient biomimetic synthesis of pyrrolo[1,2-a]indoles using a highly stereo- and regioselective [3 + 2] reaction cascade was developed and then further applied in the first total synthesis of flinderoles B and C, which proceeded in 17.2% yield over the longest linear sequence of 11 steps. 相似文献
4.
Baeza A Mendiola J Burgos C Alvarez-Builla J Vaquero JJ 《The Journal of organic chemistry》2005,70(12):4879-4882
An efficient synthesis of substituted azolopyrimidines such as pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidines, pyrimido[1,6-a]indoles, benzo[4,5]imidazo-[1,2-c]pyrimidines, an imidazo[1,2-c]pyrimidine, and pyrazolo[1,5-c]pyrimidines is described. The method involves the reaction of N-protected bromomethylazoles and tosylmethyl isocyanide (TosMIC) derivatives in nonanhydrous media. The study of the reaction conditions shows that the method is only successful under phase-transfer conditions (CH2Cl2/30% aq NaOH) using benzyltriethylammonium chloride as a catalyst. 相似文献
5.
When derivatives of 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-one or 1-carbamoylmethyl-2-methylene-2,3-dihydroindole are reacted with lithium aluminum hydride, derivatives of 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indole are formed. Under the same conditions 1-(N-phenylcarbamoylmethyl)-2-methylene-2,3-dihydroindole is not cyclized to an imidazo[1,2-a]indole. WHen treated with proton acids imidazo[1,2-a]indoles are converted to 3H-indolium salts. Opening of the imidazolidine ring is also found when imidazo[1,2-a]indole is acylated with benzoyl chloride.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 227–230, February, 1987. 相似文献
6.
A new synthetic protocol for efficient and regiospecifc assembly of indolizines and pyrido[1,2-a]indoles by coupling of substituted methyl bromides and alkynes with corresponding pyrrole-2-carboxaldehyde and 1H-indole-2-carboxaldehyde has been developed. Additionally, a possible mechanism for the reaction is proposed. 相似文献
7.
Reactions of benzotriazol-1-yl(1H-pyrrol-2-yl)methanone 10 and benzotriazol-1-yl(1H-indol-2-yl)methanone 11 with diverse ketones, isocyanates, and isothiocyanates in the presence of base afforded pyrrolo[1,2-c]oxazol-1-ones 1, oxazolo[3,4-a]indol-1-ones 2, pyrrolo[1,2-c]imidazoles 3, and imidazo[1,5-a]indoles 4 by a simple one-step procedure. 相似文献
8.
W.C. Dijksman W. Verboom D.N. Reinhoudt C.G. Hale S. Harkema G.J. van Hummel 《Tetrahedron letters》1984,25(19):2025-2028
Thermal rearrangerment of 2-vinyl-1-(1-pyrrolidinyl)benzenes varies with the leaving group ability of substituents in the vinyl moiety; compound 3 having an OR group 9-(alkoxy-methyl)pyrrolo[1,2-a]indoles and compounds 6 (X = OAc, OTs or Cl) yield 1-alkylindoles. 相似文献
9.
Reaction of 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones with dimethyl sulfate and haloalkanes in DMF or DMSO in the presence of potassium hydroxide gives the 1-substituted 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones (N-substituted products) and 9,9a-dihydro-3H-imidazo[1,2-a]indoles (O-substituted products). The latter, on treatment with acids and bases, are converted into 1-alkoxycarbonylmethyl-2,3-dihydro-1H-indoles. 1-Ethoxycarbonyl-methyl-2,3-dihydro-1H-indoles on treatment with lithium aluminohydride undergoes cyclization to 2,3,9,9a-tetrahydrooxazolo[3,2-a]indole.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 49–53, January, 1988. 相似文献
10.
Mario Frahm Thorsten von Drathen Lisa Marie Gronbach Alice Voss Felix Lorenz Jonas Bresien Alexander Villinger Frank Hoffmann Prof. Dr. Malte Brasholz 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(30):12550-12554
Tetrahydrocarbazoles and perhydrocyclohepta[b]indoles undergo a catalytic cascade singlet oxygenation in alkaline medium, which leads to chiral tricyclic perhydropyrido- and perhydroazepino[1,2-a]indoles in a single operation. These photooxygenation products are new synthetic equivalents of uncommon C,N-diacyliminium ions and can be functionalized with the aid of phosphoric acid organocatalysis. 相似文献
11.
Catalytic C-H arylation of SEM-protected azoles with palladium complexes of NHCs and phosphines 总被引:1,自引:0,他引:1
[reaction: see text] The synthesis and catalytic evaluation of palladium complexes containing imidazolyl carbene ligand of varying steric and electronic properties is reported. These complexes catalyze the efficient C-H arylation of SEM-protected azole heteroarenes and thus provide a good method for preparation of a wide range of arylated free (NH)-azoles including pyrroles, indoles, imidazoles, and imidazo[1,2-a]pyridines. The reaction is operationally simple; the complexes are insensitive to moisture. 相似文献
12.
[4 + 2]-Cycloaddition reactions between 2-vinylindoles acting as hetero-dienes and beta-acceptor substituted cyclic and acyclic enamines can be induced by formation of 2-vinylindole radical cations either via anodic oxidation or photoelectron transfer (PET) using catalytic amounts of triarylpyrylium tetrafluoroborates as sensitizers. In this way, pyrido[1,2-a]indoles or indolo[1,2-a]hexahydro-1,8-naphthyridines are formed in one step with complete regio- and stereochemical control. 相似文献
13.
A facile synthetic method of functionalized pyrrolo[1,2-a]indoles has been developed via a thermally-induced ring-opening and cyclization reaction from aniline-tethered alkylidenecyclopropanes with aldehydes. 相似文献
14.
Reaction of 1-phenylpyrazolidine with α-disubstituted aldehydes yields 10,10-disubstituted-hexahydropyrimido[1,2-a]indoles. These products represent intermediates of the Fischer Indole Synthesis which are stable under acidic conditions due to their particular substitution pattern. The following aldehydes were used: isobutyraldehyde, cyclohexanecar☐aldehyde and 4-formyl-hexanoate. However, when 5-norbornene-2-car☐aldehyde is reacted with 1-phenylpyrazolidine the corresponding hexahydropyrimido[1,2-a]indole rearranges to a bridged indole in the presence of maleic acid. 相似文献
15.
Condensation of 2-(3-methyl-1H-indol-1-yl)ethylamine (7) with benzotriazole and formaldehyde gave 2-(1H-1,2,3-benzotriazol-1-ylmethyl)-10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole (8) in 96% yield. Nucleophilic substitutions of the benzotriazolyl group in 8 with NaBH(4), NaCN, triethyl phosphite, allylsilanes, silyl enol ether and Grignard reagents afforded novel 10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indoles 9a-i in 78-95% yields. 相似文献
16.
Photochemical reaction of methanol with 1OH-azepino[1,2-a]indoles gives three types of product derived from addition of methanol to the diene system; one of the products has undergone a skeletal rearrangement. 相似文献
17.
A general, catalytic method for the diastereoselective synthesis of functionalized 1H-pyrrolo[1,2-a]indoles via an intramolecular Friedel-Crafts alkylation of N-acyl indoles is reported. Products were obtained in excellent yields (up to 98%) with high diastereoselectivities (up to >25:1 dr). 相似文献
18.
Cyclization of pyrrolidinocarboxamide derivative of 2-(1-pyrrolyl) benzoic acid leads to an imminium salt which conduct to N-substituted 9-imino (and amino) 9H-pyrrolo[1,2-a]indoles. 相似文献
19.
The chiral phosphoric acid catalyzed asymmetric[3+2]annulation of substituted 2-vinylindoles with azlactones has been established.This reaction represented a practical approach for the synthesis of structurally diverse pyrrolo[1,2-a]indoles with two vicinal stereocenters including one tetrasubstituted stereocenter in good yields and good stereoselectivities under mild conditions. 相似文献
20.
Indole 2-carboxamide derivatives 4 underwent palladium-catalyzed intramolecular cyclization reactions to afford beta-carbolinones or pyrazino[1,2-a]indoles according to different reaction pathways. The complete regioselectivity of the reactions was obtained in different reaction conditions. 相似文献