期刊
MONATSHEFTE FUR CHEMIE
卷 150, 期 7, 页码 1275-1288出版社
SPRINGER WIEN
DOI: 10.1007/s00706-019-02421-7
关键词
Green chemistry; Heterocycles; One-pot synthesis; Cycloaddition; Azoalkenes; Nitrosoalkenes
资金
- Portuguese Agency for Scientific Research, Fundacao para a Ciencia e a Tecnologia (FCT) [UID/QUI/00313/2019]
- Ministerio de Economia, Industria y Competitividad (MINECO) [CTQ-2015-67871R]
- Gobierno Vasco (GV) [IT 992-16]
- FCT [SFRH/BD/130198/2017]
- Fundação para a Ciência e a Tecnologia [SFRH/BD/130198/2017] Funding Source: FCT
For the first time, the use of natural deep eutectic solvents (NADES) as reaction media to carry out hetero-Diels-Alder reactions is disclosed. This allowed to improve the efficiency and sustainability of the synthetic approach to bis(indolyl)methanes (BIMs) based on bis-hetero-Diels-Alder/conjugate addition reactions of nitroso- and azoalkenes with indoles. The ternary mixture of H2O with choline chloride/glycerol allowed the tuning of the physical properties of this NADES leading to a better solvent system, affording the target hydroxyiminomethyl- and hydrazonomethyl-BIMs, in much shorter reaction times, higher efficiency and easier isolation procedures. Furthermore, the direct access to carbonyl-BIMs was possible when 3-methyl-1-tert-butoxycarbonyl azoalkenes were used. [GRAPHICS] .
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