Cobalt-Catalyzed One-Pot Three-Component Coupling Route to β-Acetamido Carbonyl Compounds:  A General Synthetic Protocol for γ-Lactams

Abstract

An efficient improved procedure for the synthesis of beta-acetamido carbonyl compounds is developed by a cobalt(II) chloride-catalyzed three-component coupling protocol. The procedure is also amenable to the synthesis of gamma-lactams by a three-component coupling reaction with use of 2-carbomethoxybenzaldehyde. The beta-acetamido carbonyl compounds derived from 2-carbomethoxybenzaldehyde are useful intermediates as they can be transformed to the corresponding gamma-lactams on treatment with base.

Efficient Synthesis of β-Acetamido Ketones by Silver(I) Triflate-Catalyzed Multicomponent Reactions

“…10 Recently, another new procedure for the formation of β-acetamido ketones through the MCRs of acetophenone, arylaldehyde, and acetyl chloride in acetonitrile has been developed. [11][12][13][14][15][16][17][18][19][20][21] This reaction has been extensively studied with the use of a variety of catalysts and reagents such as 20 and Amberlyst-15.…”

Melamine Trisulfonic Acid as a Highly Efficient and Reusable Catalyst for the Synthesis of β‐Acetamido Ketones

“…β-Acetamido ketones are useful building blocks for a number of biologically and pharmaceutically valuable compounds [1][2][3][4][5][6][7] . For example, they are precursors of molecules such as 1,3-amino alcohols [1][2][3] and γ-lactams 4 , as well as biologically attractive compounds such as nikkomycins or neopolyoxins 5,6 .…”

“…For example, they are precursors of molecules such as 1,3-amino alcohols [1][2][3] and γ-lactams 4 , as well as biologically attractive compounds such as nikkomycins or neopolyoxins 5,6 . Moreover, it is reported that β-acetamido ketones can act as aglucosidase inhibitors 7 .…”

“…Some catalysts have been utilized to perform this transformations, e.g. La(OTf) 3 7 , CoCl 2 8 , heteropolyacids 9 , Zr(HSO 4 ) 4 10 , K 5 16 , and CeCl 3 ·7H 2 O 17 . β-Acetamido ketones have been also prepared from acetophenones, aldehydes and amides 18 .…”

Silica Supported Tungstosilicic Acid as an Efficient and Reusable Catalyst for the One-Pot Synthesis of β-Acetamido Ketones via a Four-Component Condensation Reaction

“…30 Iqbal and coworkers reported the best known route for the synthesis of β-acetamido carbonyl compounds in the one-pot condensation of an aldehyde, an enolizable ketone, acetyl chloride, and acetonitrile catalyzed both CoCl2 31 and Montmorillonite K-10 clay. 32 A few catalysts have already been applied for the synthesis of β-acetamido ketones using this method, including Sn(II), 33 41 and Nafion-H. 42 The role of these acidic catalysts is activation of the carbonyl group of the aldehyde toward the addition of acetonitrile 43,44 or toward the attack of the enole of aryl ketone.…”