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FeCl 3 ‐Mediated Three‐Component Cascade Reaction: An Effective Approach to the Construction of Highly Functionalized Pyrrolo[1,2‐ c ]quinazolinones
Author(s) -
Zheng HuFei,
Yu ZhiHua,
Yuan Wei,
Tang ZiLong,
Clough John,
Gu YuCheng,
Shi DeQing
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304028
Subject(s) - quinazolinone , intramolecular force , cycloaddition , cascade reaction , combinatorial chemistry , cascade , chemistry , nucleophile , reagent , component (thermodynamics) , substrate (aquarium) , computational chemistry , organic chemistry , catalysis , physics , chromatography , thermodynamics , oceanography , geology
Abstract An unexpected FeCl 3 ‐mediated three‐component cascade reaction has been used to construct structurally diverse pyrrolo[1,2‐ c ]quinazolinone derivatives with potential biological activities. This method has advantages of mild conditions, simple work‐up, as well as wide substrate scope, which makes it a powerful approach to the synthesis of diverse pyrrolo[1,2‐ c ]quinazolinones. This cascade reaction involves 1,3‐dipolar cycloaddition between azomethine ylides and allenoates, followed by intramolecular nucleophilic addition in the presence of FeCl 3 . The obtained products could be easily transformed into derivatives with the pyrrolo[2,3‐ c ]quinazoline alkaloid skeleton.