Abstract
Pyrrole and its polysubstituted derivatives are important five-membered heterocyclic compounds, which exist alone or as a core framework in many pharmaceutical and natural product structures, some of which have good biological activities. The Van Leusen [3+2] cycloaddition reaction based on tosylmethyl isocyanides (TosMICs) and electron-deficient compounds as a substrate, which has been continuously developed due to its advantages such as operationally simple, easily available starting materials, and broadly range of substrates, is one of the most convenient methods to synthetize pyrrole heterocycles. In this review, we discuss the different types of two carbon synthons in the Van Leusen pyrrole reaction and give a summary of the progress of these synthesis methods in the past two decades.
Highlights
Pyrrole and its polysubstituted derivatives are important five-membered heterocyclic compounds, which exist alone or as a core skeleton in many pharmaceutical and natural product structures, some of them have good bioactivity such as antibacterial [1,2], antifungal [3,4], anti-inflammatory [5,6], antiviral [7], antimalarial [8], anticancer [9,10], antiparasitic [11], etc., and can be used as enzyme inhibitor in the organism [12,13]
Since pyrrole and its multi-substituted derivatives play an important role in organic synthesis as well as in biology, syntheses of five-membered heterocyclic pyrrole compounds have always been valued by researchers
Leusen and co-workers firstly reported that tosylmethyl isocyanides (TosMICs) can react with electron-deficient found that there are cycloadditions occurring in alkenes with different electrondeficient alkenes under basic conditions to produce
Summary
Pyrrole and its polysubstituted derivatives are important five-membered heterocyclic compounds, which exist alone or as a core skeleton in many pharmaceutical and natural product structures, some of them have good bioactivity such as antibacterial [1,2], antifungal [3,4], anti-inflammatory [5,6], antiviral [7], antimalarial [8], anticancer [9,10], antiparasitic [11], etc., and can be used as enzyme inhibitor in the organism [12,13]. There are many methods for synthesizing pyrrole compounds in laboratory routes [14], and the classical methods include Knorr pyrrole synthesis [15], Paal-Knorr pyrrole synthesis [16], Hantzsch pyrrole synthesis [17], Barton-Zard reaction [18], Van Leusen pyrrole synthesis [19], and Piloty–Robinson pyrrole synthesis [20]. These synthesis methods are summarized in Scheme 1. Some typical pyrrole derivative chemical structures and thephysiological physiological functions
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