Multicomponent Reactions Accelerated by Aqueous Micelles

Abstract

Multicomponent reactions are powerful synthetic tools for the efficient creation of complex organic molecules in an one-pot one-step fashion. Moreover, the amount of solvents and energy needed for separation and purification of intermediates is significantly reduced what is beneficial from the green chemistry issues point of view. This review highlights the development of multicomponent reactions conducted using aqueous micelles systems during the last two decades.

Keywords: micelles; multicomponent reactions; on water reaction; surfactants; water.

Figure 1

Schematic representation of two types of micellar catalysis summarized in this review in respect to classical approach for MCRs.

Scheme 1

Comparison of Mannich-type reaction proceeded in aqueous micellar solution vs. organic solvent.

Scheme 2

An unusual Mannich type reaction of indole reported by Kumar et al. (2013).

Scheme 3

Mannich-type reaction with tertiary aromatic amines.

Scheme 4

The Biginelli reaction.

Scheme 5

The Passerni (above) and the Ugi (below) reactions.

Scheme 6

The Kabachnik-Fields reaction.

Scheme 7

The Strecker reaction under micellar catalysis type 2 conditions.

Scheme 8

Micelles promoted synthesis of β-lactames via Kinugasa reaction.

Scheme 9

Micelles promoted synthesis of dihydropyridines 15 via Hantzsch reaction.

Scheme 10

Micelles and ultrasonic promoted synthesis of polyhydroquinoline derivatives 18 via unsymmetrical Hantzsch reaction.

Scheme 11

Micelles promoted synthesis of pyridine derivatives 16 via unsymmetrical Hantzsch reaction.

Scheme 12

Structures of compounds 17-28 obtained via MCRs in aqueous micellar solutions.

Scheme 13

Structures of compounds 29-46 obtained via MCRs in aqueous micellar solutions.

Scheme 14

Structures of compounds 47-51 obtained via MCRs in aqueous micellar solutions.