Synthesis of 2-amino-3-cyano 4-H-chromenes containing quinoline in water: computational study on substituent effects
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- 作者：Majid M. Heravi ; Tayebeh Hosseinnejad…
- 关键词：Chromene ; 2 ; Chloroquinoline ; 3 ; carbaldehyde ; Water ; Density functional theory ; Electron density properties ; Quantum theory of atoms in molecules
- 刊名：Journal of the Iranian Chemical Society
- 出版年：2017
- 出版时间：April 2017
- 年：2017
- 卷：14
- 期：4
- 页码：823-832
- 全文大小：
- 刊物主题：Analytical Chemistry; Inorganic Chemistry; Physical Chemistry; Biochemistry, general; Organic Chemistry;
- 出版者：Springer Berlin Heidelberg
- ISSN：1735-2428
- 卷排序：14
文摘
An efficient, high yielding and environmentally benign strategy to the synthesis of new 2-amino-3-cyano-4-H-chromene derivatives, via one-pot three-component reaction involving malononitrile, various α- or β-naphthol and appropriate aromatic aldehydes including 2-chloroquinoline-3-carbaldehydes in the presence of morpholine in water, was achieved. During the development of the synthesis five new chromene derivatives were fruitfully synthesized. It was found that employing this approach, aromatic aldehydes bearing electron-withdrawing groups give higher yields of the corresponding products in shorter reaction times. This observation was in agreement with topological analysis of calculated electron density functions using density functional theory and quantum theory of atoms in molecules approaches.