Applications of Multicomponent Reactions for the Synthesis of Diverse Heterocyclic Scaffolds

Abstract

The sequencing of multicomponent reactions (MCRs) and subsequent cyclization reactions is a powerful stratagem for the rapid synthesis of diverse heterocyclic scaffolds. The optimal MCR is sufficiently flexible that it can be employed to generate adducts bearing a variety of functional groups that may then be selectively paired to enable different cyclization manifolds, thereby leading to a diverse collection of products. The growing interest in diversity-oriented synthesis has led to increased attention to this paradigm for library synthesis, which has inspired many advances in the design and implementation of MCRs for the construction of diverse heterocyclic scaffolds.

Selective Synthesis and Structural Confirmation of 1,3‐Oxazines and Schiff Bases with Controllable Substitution Patterns

“…We have successfully prepared many such scaffolds by using multicomponent reactions (MCRs). [1][2][3][4][5][6][7] MCRs are now being tailored and fine tuned for the synthesis of various heterocyclic scaffolds. The Mannich reaction is one of the most important MCRs, and onepot MCRs have emerged as an effective method for atom economic and environmentally benign synthesis.…”

“…This is because of their convergence, high yield, facile execution, and ability to generate diverse sets of compounds with easily available starting materials in just in a single operation. [1][2][3][4][5][6][7] An extension to the Mannich reaction is the Betti approach, in which the replacement of an active methylene compound (ketone) by an electron-rich aromatic compound, 2-naphthol, leads to the synthesis of a-aminobenzylnaphthols. The preparation of substituted Betti bases (aminobenzyl derivatives) in this way is considerably advantageous because the C À C bond is formed under mild reaction conditions.…”

Synthesis of Isoxazolopyridines and Spirooxindoles under Ultrasonic Irradiation and Evaluation of Their Antioxidant Activity

“…These reactions have enormous effectiveness, particularly for the construction of heterocyclic compounds which exhibit a wide range of biological activities [2][3][4][5]. Multicomponent reactions proceed in accordance with green chemistry principles in terms of a high degree of atom economy, easier progress of reactions, decreased reaction times, lack of waste products, and low power consumption [6,7].…”

Asymmetric Catalysis: Resin‐Bound Hydroxyprolylthreonine Derivatives in Enamine‐Mediated Reactions

“…Richard D. Carpenter, James C. Fettinger, Kit S. Lam, and Mark J. Kurth* Control of relative and absolute stereochemistry with stepeconomy [1,2] presents a continuing challenge in organic synthesis. [3] Asymmetric crossed aldols have historically involved chiral auxiliaries or O-trapped organometallic intermediates; the latter operate by either a Zimmerman-Traxler or an open transition-state model.…”