- An intermolecular C-H oxidizing strategy to access highly fused carbazole skeletons from simple naphthylamines
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Highly π-extended hetero-cyclic/aromatic skeletons are of great importance as they can be utilized in many organic material based technologies. Therefore, developing efficient, pre-activation-free, synthetic procedures for the rapid build-up of these complex structures remains a high priority objective. The herein presented approach delivers highly fused carbazole skeletons from simple naphthylamine derivatives.
- Rank, Christian K.,Jones, Alexander W.,Wall, Tatjana,Di Martino-Fumo, Patrick,Schr?ck, Sarah,Gerhards, Markus,Patureau, Frederic W.
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supporting information
p. 13749 - 13752
(2019/11/19)
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- Facial and practical synthesis of benzimidazole-based N-heterocyclic carbenes
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An efficient synthesis of benzimidazole-based N-heterocyclic carbenes has been developed. The key step in this synthetic methodology was a one-pot protocol for the synthesis of N,N′-diarylaryldiamines starting from aryldiamine and aryl halides.
- Wang, Han,Xia, Yuyu,Lv, Shang,Xu, Jingli,Sun, Zhihua
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supporting information
p. 2124 - 2127
(2013/05/08)
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- Copper(II)-mediated oxidative coupling of 2-aminonaphthalene homologues. Competition between the straight dimerization and the formation of carbazoles
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Whereas the Cu(II)-mediated oxidative coupling of 2-aminonaphthalenes 7a and 7b results in the clean formation of 1,1′-binaphthyls 13a and 13b, respectively, their higher homologues and congeners 8 - 12 have been found to exhibit a different reaction pattern. Thus, 2-aminoanthracene (8) gave a ~1:1 mixture of the expected bianthryl derivative 15 and the carbazole 16, whereas the 9-aminophenanthrene (10), 3-phenyl-1-aminonaphthalene (11), and 2-aminochrysene (12) produced almost exclusively the corresponding carbazoles 19, 20, and 21, respectively. By contrast, the isomeric 3-aminophenanthrene (9) gave rise to the azo compound 17 as a result of the preferential oxidation on the nitrogen. The carbazoles have been shown to arise directly from the coupling reactions rather than from the primarily formed binaphthyls. Alternatively, carbazole 19 can also be prepared from 1b on reaction with hydrazine. On the other hand, treatment of 3a with hydrazine resulted in the formation of a ~2:7 mixture of amine 11 and arylhydrazine 22. 2,2′-Diamino-1,1′-bianthryl (15) has been resolved into enantiomers via Cocrystallization with (-)-N-benzylcinchonidinium chloride and shown to have (R)-(-)-15 configuration by X-ray crystallography.
- Vyskocil,Smrcina,Lorenc,Tislerova,Brooks,Kulagowski,Langer,Farrugia,Kocovsky
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p. 1359 - 1365
(2007/10/03)
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- Selective Cross-Coupling of 2-Naphthol and 2-Naphthylamine Derivatives. A Facile Synthesis of 2,2',3-Trisubstituted and 2,2',3,3'-Tetrasubstituted 1,1'-Binaphthyls
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The novel 1,1'-binaphthyls with OH and/or NHR (R = H or Ph) groups in the 2,2'-positions and with additional methoxycarbonyl group(s) in the 3- or 3,3'-positions (13-18) have been synthesized from their respective precursors 1-5 by the CuCl2/t-BuNH2-mediated oxidative cross-coupling.In most cases, the chemoselectivity was good, and the cross-coupled products 11-18 were obtained in fair to excellent yields.Binaphthyls 6-10, resulting from the selfcoupling, and carbazoles 19-23 have been identified as byproducts.Ab initio calculations and electrochemical measurements have been employed to account for the observrd selectivity.
- Smrcina, Martin,Vyskocil, Stepan,Maca, Bohumil,Polasek, Miroslav,Claxton, Thomas A.,et al.
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p. 2156 - 2163
(2007/10/02)
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- Reactivity and Structure of N-Phenyl-1-naphthylamines and Related Compounds. Part 3. Reaction with Oxygen-centred Radicals
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Comparison is made between products obtained by oxidation of N-phenyl-1-naphthylamines and 1-naphthyl phenyl nitroxides with peroxyl radicals.It is concluded that oxidation of the amines does not proceed to a considerable extent via the nitroxides.Comparison is also made of products obtained from these amines and nitroxides by oxidation with Fremy's salt.
- Forrester, Alexander R.,Fullerton, Joseph D.,McConnachie, Gordon
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p. 2711 - 2715
(2007/10/02)
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- Nitroxide Radicals. Part 21. Spontaneous Decomposition of N-Aryl 1- and 2-Naphthyl Nitroxides
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N-Aryl 1-naphthyl nitroxides self-react in solution to give the corresponding secondary amines and N-aryl-1,4-naphthoquinone imines.When reaction at the 4-naphthyl position is hindered by substituents benzoquinone imines are also produced.N-Phenyl 2-naphthyl nitroxide under similar conditions gives the corresponding amine and 2-phenylamino-1,4-naphthoquinone via a 1,2-naphthoquinone imine N-oxide intermediate.
- Forrester, Alexander R.,Fullerton, Joseph D.,McConnachie, Gordon
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p. 1759 - 1764
(2007/10/02)
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