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Atom‐economical Approaches to 1,5‐Benzodiazepines Containing Indole Ring via Fe 3 O 4 @SiO 2 ‐PTSA‐catalyzed Multi‐component Domino Reactions
Author(s) -
Zhang KaiYue,
Li Jing,
Wang KaiXuan,
An Xiaoying,
Wang LanZhi
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202003903
Subject(s) - indole test , catalysis , diazepine , ring (chemistry) , domino , chemistry , cascade reaction , atom (system on chip) , alkyl , atom economy , combinatorial chemistry , aryl , ethanol , medicinal chemistry , organic chemistry , computer science , embedded system
Four novel atom‐economical approaches for synthesis of 1,5‐dihydrospiro[benzo[ b ][1,4]diazepine‐2,3′‐indole] compounds via three‐component or four‐component domino reactions have been developed in the presence of a catalytic amount of magnetic nanoparticles (Fe 3 O 4 @SiO 2 ‐PTSA) in ethanol, which provide an efficient one‐pot synthesis of 1,5‐benzodiazepines with multi‐ring system and functional groups containing indole, aryl, ester, acyl and alkyl groups in excellent yields. In a one‐pot operation, two new nitrogen heterocycle (indole and diazepine) rings and four new chemical bonds (one C−C, two C−N and one C=C) were constructed by series of domino reactions. Furthermore, plausible catalytic synthesis reaction mechanisms have been proposed. The advantages of these methods are the green reaction process, the recyclable magnetic catalyst, mild reaction conditions, short reaction time and high yields of products.