A general access to 1,1-cyclopropane aminoketones and their conversion into 2-benzoyl quinolines

Abstract

1,1-Cyclopropane aminoketones were efficiently synthesized in high yields by the tandem reaction of α-amino aryl ketones with vinyl sulfonium salts using DBU as the base in CH(2)Cl(2). This methodology was utilized to synthesize 2-benzoyl quinolines.

An Efficient Method for the Synthesis of 2′,3′-Nonsubstituted Cycloalkane-1,3-dione-2-spirocyclopropanes Using (2-Bromoethyl)diphenylsulfonium Trifluoromethanesulfonate

“…In 2012, Lin and colleagues reported a simple and efficient access to 1,1-cyclopropane aminoketones 12 via the reaction of α-aminoacetophenones 10 and vinylsulfonium salt 11 in the presence of 1,8-diazabicyclo [5.4.0]-undec-7-ene (DBU) 16) (Chart 4). The vinylsulfonium salt 11 was prepared from (2-bromoethyl) diphenylsulfonium trifluoromethanesulfonate (13) [17][18][19][20][21] by eliminating the hydrogen bromide with a base such as silver(I) oxide, 17,18) potassium bicarbonate, 19,22) or sodium hydride (NaH).…”

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

“…The group of Lin investigated the cyclopropanation of aminoketones using substituted vinylsulfonium salts 492 , with high cis -selectivity observed for β-phenyl-substituted vinyl moieties (Scheme 82a). 306 In a related study, Chandrasekaran et al investigated the scope of cyclopropanation using substituted 2-bromosulfonium salts ( 395 ) (Scheme 82b). 307 The use of unsymmetrical active methylene nucleophiles led to very good diastereomeric ratios, however, with higher substituted homologues, both reactivity and diastereoselectivty decreased significantly.…”

Synthesis of α‐Aminocyclopropyl Ketones and 2‐Substituted Benzoimidazoles from 2‐Hydroxycyclobutanones and Aryl Amines

“…[1,2] Within this family, α-aminocyclopropyl ketones are much less developed. One recent method for the construction of such compounds involves the reaction of α-arylamino ketones and vinyl sulfonium salts in the presence of DBU, [3] while more traditional approaches require multistep procedures [4] (Scheme 1). In the pursuit of our investigations of the reactions of 2hydroxycyclobutanone with amines, [5,6] we envisaged that the condensation of a 2-substituted-2-hydroxycyclobutanone 1 with an aniline might provide an attractive route to α-aminocyclopropyl ketones 3, taking advantage of the α-iminol rearrangement [7] of a transient 2-substituted-2-hydroxycyclobutyl imine A (Scheme 1).…”