- Nickel-Catalyzed Synthesis of N-Substituted Pyrroles Using Diols with Aryl- and Alkylamines
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Herein, nickel-catalyzed sustainable strategy for the synthesis of N-substituted pyrroles using butene-1,4-diols and butyne-1,4-diols with a series of aryl-, alkyl-, and heteroarylamines is reported. The catalytic protocol is tolerant of free alcohol, halide, alkyl, alkoxy, oxygen heterocycles, activated benzyl, and the pyridine moiety and resulted in up to 90% yield. Initial mechanistic studies involving defined nickel catalyst, determination of rate, and order of reaction including deuterium-labeling experiments were performed for pyrrole synthesis.
- Singh, Khushboo,Kabadwal, Lalit Mohan,Bera, Sourajit,Alanthadka, Anitha,Banerjee, Debasis
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p. 15406 - 15414
(2019/01/04)
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- Reaction of pyrroles with naphthoquinones. Synthesis of new pyrrolylnaphthoquinone dyes
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The reaction of 1,4-naphthoquinone (1) with N-alkylpyrroles (2) gives a mixture of 2-(pyrrol-2-yl)-1,4-naphthoquinones (3) and 2,5-bis(1,4-naphthoquinon-2-yl)pyrroles (4). The yields and the ratios of these two products depend greatly on the experimental conditions. The reaction has been extended to 5-hydroxy-1,4-naphthoquinone (juglone, 5) and 1,2-naphthoquinone (6). New pyrrolylnaphthoquinones are obtained.
- Lion,Baudry,Hedayatullah,Da Conceicao,Hocquaux,Genard,Maignan
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p. 1635 - 1640
(2007/10/03)
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- Remarkable fast n-alkylation of azaheterocycles under microwave irradiation in dry media
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Under microwave irradiation a number of azaheterocycles (i.e., pyrrole, imidazole, pyrazole, indole, and carbazole) react remarkably fast with alkyl halides to give exclusively N-alkyl derivatives.
- Bogdal, Dariusz,Pielichowski, Jan,Jaskot, Krzysztof
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p. 715 - 722
(2007/10/03)
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- A new route to N-substituted heterocycles
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N-(Benzotriazol-1-ylmethyl)-indole, - pyrrole, -carbazole, and -benzimidazole, and analogs substituted in the methylene group are converted by lithium aluminum hydride, or by Grignard reagents, or in two cases by organozinc reagents, into the N-substituted heterocycles in good yields.
- Katritzky, Alan R.,Lang, Hengyuan,Lan, Xiangfu
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p. 2829 - 2838
(2007/10/02)
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