An acid-catalyzed 1,4-addition isocyanide-based multicomponent reaction in neat water

A green 1,4-addition isocyanide-based three-component reaction was developed to synthesize chromanones via a facile, mild, and efficient one-pot protocol without a metal catalyst. The 1,4-addition of isocyanides occurred at the C-2 position of chromones instead of the Schiff base in neat water. We f...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 22; no. 12; pp. 3716 - 3720
Main Authors Lei, Jie, Li, Yong, Xu, Jia, Tang, Dian-Yong, Shao, Jing-Wei, Li, Hong-yu, Chen, Zhong-Zhu, Xu, Zhi-Gang
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 22.06.2020
Royal Society of Chemistry
Subjects
Alkenes
Catalysts
catalytic activity
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Crystallography
Green & Sustainable Science & Technology
Green chemistry
hydrogen bonding
Hydrogen bonds
Imines
Physical Sciences
schiff bases
Science & Technology
Science & Technology - Other Topics
FUNCTIONALIZATION
CHEMISTRY
CHROMONE
PYRROLES
DERIVATIVES
UGI
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Summary:A green 1,4-addition isocyanide-based three-component reaction was developed to synthesize chromanones via a facile, mild, and efficient one-pot protocol without a metal catalyst. The 1,4-addition of isocyanides occurred at the C-2 position of chromones instead of the Schiff base in neat water. We found that the hydrogen bond can dictate the stereo-outcome of olefins, providing an effective method for the diastereomer-selective synthesis of this type of chromanone. The novel green synthetic protocol allowed the quick synthesis of complex chromanones in an environmentally friendly manner.
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ISSN:1463-9262
1463-9270
1463-9270
DOI:10.1039/D0GC00652A