Xanthenedione Substituted Metallophthalocyanines as an Efficient and Recyclable Catalyst for One–pot Three Component Synthesis of 3‐Substituted Indoles

Abstract

An efficient one-pot methodology for the synthesis of 3-aminoalkylated indoles catalyzed by metallophthalocyanines has been developed via a three component Mannich type reaction with secondary amines, aldehydes and indoles. The newer catalysts i. e. metallophthalocyanines were synthesized by tetramerization of xanthenedione substituted phthalonitrile in anhydrous N,N-dimethylformamide by conventional heating and microwave conditions and were characterized by different spectroscopic techniques. The aggregation behaviors of these metallophthalocyanines were studied at different concentration in dimethyl sulfoxide and it was observed that these metallophthalocyanines show monomeric behavior in DMSO. The catalyst was separated from the reaction medium, characterized and was successfully reused up to five catalytic cycles. It was observed that the catalyst is stable in the catalytic system. Based on observations, a suitable reaction pathway is proposed for the current reaction.

Recent Advances of Three‐component Reactions of Simple Indoles

“…Reactions of secondary amines, aldehydes and indoles would afford novel condensation products via the C−N bond formation. Diverse secondary amines, such as N ‐methylhidine, [29a–e] hexapyrrole, [29b] morpholine [29b,c] and tetrahydroxopyrrole, [29b,c] have been studied during these years. For example, the use of elemental iodine (10 mol%) [29e] was able to achieve these reactions efficiently with good yields (80–96%) (Scheme 21).…”

Recent Advances in the Use of CoPc-MWCNTs Nanocomposites as Electrochemical Sensing Materials

“…Recently, metal phthalocyanines (MPcs) have received much interest in the field of catalysis. The high catalytic activity of metal phthalocyanine is attributed to the central metal ions [ 6 , 27 ]. Among these MPcs, cobalt phthalocyanine (CoPc) is one of the bright catalysts for varied organic reactions because of its high activity and selectivity of oxidation processes [ 6 , 28 , 29 , 30 ].…”

Investigation of photocatalytic properties of cobalt phthalocyanines on benzyl alcohol photoxidation

“…Due to their thermal, chemical and light stability, [1,2] metal phthalocyanines (MPcs) have been widely used in many fields, including commercial pigments, [3,4] chemical sensors, [5][6][7][8] security devices, [9] information storage, [10] electrocatalytic reagents, [11][12][13][14] and photodynamic therapy. [15][16][17][18] In recent years, MPcs have attracted considerable attention in catalysis fields [19][20][21][22][23][24] due to the high catalytic activity of MPc can be related to the central metal ions. In order to understand the important function of coordination compounds in catalytic reactions during industrial processes carried out on an industrial scale, it is necessary to learn the exact mechanisms of the reactions carried out.…”