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A polyoxometalate immobilized on MOF‐5 (POM/MOF‐5) material has been synthesized and evaluated for the diversity‐oriented synthesis of poly‐functionalized 3‐pyrrolin‐2‐ones via pseudo‐four‐component reaction between dialkyl acetylenedicarboxylate, amines, and aldehyde. The catalyst can be separated from the reaction mixture and reused at least five...
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... There are three universal strategies towards ADPs enabling their synthesis with a wide range of substituents (Scheme 1). These strategies are the substitution of hydroxyl groups in the corresponding HDPs via their reactions with amines (pathway a) [1,2,7,[9][10][11][12], the multicomponent reactions of amines and aldehydes with pyruvic acid derivatives (pathway b) [13,14] or acetylenedicarboxylates (pathway c) [15,16] (Scheme 1). ...
... There are three universal strategies towards ADPs enabling their synthesis with a wide range of substituents (Scheme 1). These strategies are the substitution of hydroxyl groups in the corresponding HDPs via their reactions with amines (pathway a) [1,2,7,[9][10][11][12], the multicomponent reactions of amines and aldehydes with pyruvic acid derivatives (pathway b) [13,14] or acetylenedicarboxylates (pathway c) [15,16] (Scheme 1). Scheme 1. Retrosynthetic pathways towards ADPs. ...
... There are three universal strategies towards ADPs enabling their synthesis with wide range of substituents (Scheme 1). These strategies are the substitution of hydroxy groups in the corresponding HDPs via their reactions with amines (pathway a) [1,2,7,9 12], the multicomponent reactions of amines and aldehydes with pyruvic acid derivative (pathway b) [13,14] or acetylenedicarboxylates (pathway c) [15,16] Then, we performed a series of reactions of compound 1a with cyclohexylamine (Table 1) in order to obtain the required cyclohexylamino derivative 3a. The examined conditions (Table 1) were selected according to the previously reported substitution reactions of hydroxyl groups in various non-spiro HDPs (bearing hydrogen and a substituent at the C 5 position) with amines [1,2,7,[9][10][11][12]. ...
The 3-hydroxy-1,5-dihydro-2H-pyrrol-2-one motif is a valuable scaffold in drug discovery. The replacement of the 3-oxy fragment in 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones-based compounds with a 3-amino one (3-amino analogs of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones, 3-amino-1,5-dihydro-2H-pyrrol-2-ones) can play a crucial role in their biological effect. Thus, approaches to 3-amino-1,5-dihydro-2H-pyrrol-2-ones are of significant interest. We developed an approach to 5-spiro-substituted 3-amino-1,5-dihydro-2H-pyrrol-2-ones that could not be obtained using previously reported approaches (reactions of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones with amines). The developed approach is based on the thermal decomposition of 1,3-disubstituted urea derivatives of 5-spiro-substituted 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones, which were prepared via their reaction with carbodiimides.
Schiff base Mo(VI) Complexes have been grafted onto different generations of diethanolamine branched Merrifield resin through several step of substitution reactions and used as heterogeneous catalyst to synthesize pyrrolin-2-ones from...
Dialkyl acetylenedicarboxylates (DAAD) are the class of acetylenic compounds that are broadly used in organic synthesis in a noticeable quantity. Their wide application has made them an important moiety in heterocyclic compounds and drug discovery programs. Dialkyl acetylenedicarboxylate is a di‐ester in which the ester groups are conjugated with a carbon‐carbon triple bond. As such, the molecule is very electrophilic, and is broadly used as a dienophile in various cycloaddition reactions, for example the Diels‐Alder reaction. In addition, it is a strong Michael acceptor. Due the importance of dialkyl acetylenedicarboxylate in organic synthesis, we are trying to show the applications of this compound in the synthesis of different heterocycles using multicomponent reactions. In this review, we show recent advances (2016–2022) for the synthesis of various heterocycles that have different ring sizes (five, six and seven membered, Spiro and fused heterocycles), using DAAD via multicomponent reactions.
The chapter describes and thematically summarizes applications of environmentally benign heterogeneous catalysts for a wide range of multicomponent reactions in the 1996–2021 period. Examples include the well-known carbonyl-based Hantzsch and Biginelli multicomponent reactions as well as the isocyanide-based Passerini and Ugi or Groebke-Blackburn-Bienaymé multicomponent reactions. A broad array of green methods for the preparation of biologically active compounds such as quinoline derivatives, pyridine derivatives and other heterocycles, and peptidomimetics is included.
