共查询到20条相似文献,搜索用时 15 毫秒
1.
The formation of pyridines via a crossed [2 + 2 + 2] cycloaddition has been achieved on a solid-support for the first time. 相似文献
2.
A highly convergent [2+2+2] cyclotrimerization approach to anthracenes and 2-azaanthracenes has been developed. It allows for the facile introduction of the anthracene moiety on alkyne and nitrile bearing molecules and the rapid construction of compound arrays. This is showcased in the assembly of a collection of fluorophores and their photochemical evaluation. 相似文献
3.
A concise synthesis of phenanthridines via a microwave-assisted [2+2+2] cyclotrimerization reaction has been developed. 相似文献
4.
Generally, synthesis of hydantoin derivatives involve use of carbonyl compounds which in turn require multistep synthesis. Here, we report a new approach to assemble spirohydantoins via [2+2+2] cyclotrimerization reaction using commercially available, inexpensive hydantoin as a starting material. 相似文献
5.
Macrocyclization via rhodium-catalyzed intramolecular [2 + 2 + 2] annulation of triynes has been explored in an aqueous-organic biphasic system. The biphasic system controls the concentration of hydrophobic substrates in the aqueous reaction phase and offers diluted reaction conditions without the use of a slow addition technique. The system also achieves selective cross-annulation between hydrophobic diynes and hydrophilic alkynes. 相似文献
6.
Boñaga LV Zhang HC Moretto AF Ye H Gauthier DA Li J Leo GC Maryanoff BE 《Journal of the American Chemical Society》2005,127(10):3473-3485
We investigated the formation of macrocycles from alpha,omega-diynes in cobalt-mediated co-cyclotrimerization reactions. Long-chain alpha,omega-diynes underwent metal-mediated [2 + 2 + 2] cycloadditions with nitriles, cyanamides, or isocyanates in the presence of CpCo(CO)2 (Cp = cyclopentadienide) to yield pyridine-containing macrocycles, i.e., meta- and para-pyridinophanes, such as 5m/5p, 35m/35p, and 41m/41p. The regioselectivity of these reactions was affected by the length and type of linker unit between the alkyne groups, as well as by certain stereoelectronic factors. An analogous alpha,omega-cyano-alkyne, 28, combined with an alkyne to yield two isomeric meta-pyridinophanes, such as 5m and 29m, and an ortho cycloadduct (benzannulation product), such as 29o. We developed a reaction protocol for these cobalt-based [2 + 2 + 2] cycloadditions that involves markedly improved conditions such that this process offers a convenient, flexible synthetic approach to macrocyclic pyridine-containing compounds. For example, diyne 6 reacted with p-tolunitrile in 1,4-dioxane to give 7p and 7m (7:1 ratio) in 87% yield at a moderate temperature of ca. 100 degrees C in 24 h without photoirradiation or syringe-pump addition. Isocyanates were also effective reactants, as exemplified by the formation of 44p almost exclusively (44p:44m > 50:1) in 64% yield from diyne 8 and 2-phenylethylisocyanate. By using this improved protocol we were able to co-cyclotrimerize long-chain alpha,omega-diynes with alkynes in certain cases to demonstrate a successful macrocyclic variant of the Vollhardt reaction. For instance, diyne 6 reacted with dipropylacetylene to give paracyclophane 57p and benzannulene 57o (2:1 ratio) in 29% yield. 相似文献
7.
It found that the Ru(3)(CO)(12) coordinated with 2-(diphenylphosphino)benzonitrile (2-DPPBN) to effectively catalyze the [2 + 2 + 2] cyclotrimerization of the trifluoromethyl group substituted internal alkynes in high yields with up to >98% regioselectivity. Isolation of a ruthenacyclopentadiene was successful and confirmed that the complex is a reaction intermediate. 相似文献
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9.
Sugiyama YK Kato R Sakurada T Okamoto S 《Journal of the American Chemical Society》2011,133(25):9712-9715
A cobalt-catalyzed alkyne [2 + 2 + 2] cycloaddition reaction has been applied to polymerizations yielding linear polymers via selective cross-cyclotrimerization of yne-diyne monomers, which occurs in a chain-growth manner. Additionally, through control of the alkyne reactivity of the two monomers, this method was efficiently applied to the spontaneous block copolymerization of their mixture. Here we present the proposed mechanism of the catalyst transfer process of this cycloaddition polymerization. 相似文献
10.
Sarah R. Yong Stephen G. Pyne Alison T. Ung Brian W. Skelton Peter Turner 《Tetrahedron》2005,61(34):8120-8129
The phosphine-catalyzed [3+2]-cycloaddition of the 2-methylene γ-lactams 4 and 5 and the acrylate 6 with the ylides derived from the ethyl ester, the amide or the chiral camphor sultam derivative of 2-butynoic acid (7a-c) give directly, or indirectly after reductive cyclization, spiro-heterocyclic products. The acid 32 underwent Curtius rearrangement and then acid hydrolysis to give two novel spiro-cyclic ketones, 41 and 42. 相似文献
11.
[reaction: see text] Spirocyclic C-arylribosides were synthesized from the known gamma-ribonolactone derivative. Lithium acetylide addition followed by glycosylation with 3-(trimethylsilyl)propargyl alcohol converted the ribonolactone to silylated diynes. After desilylation or iodination, subsequent ruthenium-catalyzed cycloaddition of resultant diynes with alkynes or chloroacetonitrile gave spirocyclic C-arylribosides. 相似文献
12.
Alan R. Katritzky Zouquan Wang Jianqing Li Julian R. Levell 《Journal of heterocyclic chemistry》1997,34(4):1379-1381
1,2,3-Triarylpyrroles 7 have been synthesized by sequential lithiation and alkylation of 1-benzylbenzo-triazoles 1 with 2-bromoacetaldehyde diethyl acetal (2) and N-benzylideneaniline (4), followed by treatment with formic acid in ethanol. 相似文献
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Yamamoto Y Saigoku T Ohgai T Nishiyama H Itoh K 《Chemical communications (Cambridge, England)》2004,(23):2702-2703
In the presence of catalytic amounts of Cp*RuCl(cod), the cycloaddition of 1,6-diynes with various C-alkynylglycosides proceeded at ambient temperature to afford C-arylglycosides in 46-93% yields. 相似文献
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16.
Chelate complex 1 (5 mol%) was found to catalyze the [2 + 2 + 2] cyclization of terminal alkynes in good yields in a 80/20 mixture of water and ethanol at room temperature without further activation. 相似文献
17.
Chernov N. M. Moroz T. V. Shutov R. V. Kuz’mich N. N. Shchegolev A. E. Sopova M. V. Yakovlev I. P. 《Russian Journal of General Chemistry》2019,89(12):2463-2470
Russian Journal of General Chemistry - The effect of electronic properties of substituents in the reactants on the [4+2]-cycloaddition of 3-vinyl-chromen-4-ones (dienes) and N-vinylpyrrolidines... 相似文献
18.
Synthesis of cyclopentenyl and cyclohexenyl ketones via [3 + 2] and [4 + 2] annulations of 1,2-allenic ketones简 总被引:1,自引:1,他引:0
In this paper, an efficient synthesis of cyclopentenyl ketones and cyclohexenyl ketones through tertiary phosphine catalyzed [3 + 2] and [4 + 2] annulations of 1,2-allenic ketones with activated alkenes has been developed. Compared with published synthetic methods on cyclopentenyl ketones and cyclohexenyl ketones, the protocols developed in this paper have the advantages such as readily available starting materials, mild reaction conditions and high efficiency. 相似文献
19.
Design,Synthesis and Late-Stage Modification of Indane-Based Peptides via [2+2+2] Cyclotrimerization
Prof. Dr. Sambasivarao Kotha Naveen Kumar Gupta Dr. Gaddamedi Sreevani Dr. Nageswara Rao Panguluri 《化学:亚洲杂志》2021,16(22):3649-3657
Here, we prepared several dipeptides containing 2-aminoindane-2-carboxylic acid (Aic) and carried out further synthetic transformations. Synthesis and purification of modified peptides by using [2+2+2] cyclotrimerization is a challenging task. We are able to modify the unusual amino acids and peptide derivatives by late-stage incorporation of benzylhalo functionality. To incorporate benzylhalo moiety we used [2+2+2] cyclotrimerization in the presence of Mo(CO)6. These halo derivatives are potential substrates for further modification by Sonogashira reaction, Suzuki–Miyaura cross-coupling, sultine formation, and the Diels–Alder reaction sequence. 相似文献
20.
Jiang Y Khong VZ Lourdusamy E Park CM 《Chemical communications (Cambridge, England)》2012,48(25):3133-3135
An efficient dual synthetic manifold for 2-aminofurans and 2-unsubstituted furans has been developed. The carbenoid-mediated [3 + 2] cycloaddition of copper carbenoids with enamines provides 2-amino-2,3-dihydrofurans which serve as common intermediates for both 2-aminofurans and 2-unsubstituted furans. 相似文献