173345-91-0Relevant articles and documents
Functionalisation of pyrrolidin-2-ones at C4 and C5
Easton, Christopher J.,Pitt, Michael J.,Ward, Caroline M.
, p. 12781 - 12790 (1995)
Treatment of pyrrolidin-2-ones with N-bromosuccinamide affords the corresponding 4,5-dibromo-γ-lactans. The introduced bromo substituents may be selectively displaced in ionic and radical reactions. The synthetic utility of this procedure is illustrated in regioselective elaborations of the dibromides, including the generation of a bicyclic tetrahydrofuropyrrolidinone system.
A one pot protocol to convert nitro-arenes into: N-aryl amides
Massolo, Elisabetta,Pirola, Margherita,Puglisi, Alessandra,Rossi, Sergio,Benaglia, Maurizio
, p. 4040 - 4044 (2020/02/04)
A two-step one pot, experimentally simple protocol, based on readily available and inexpensive reagents allowed the conversion of nitro-arenes directly to N-aryl amides. A metal-free reduction of the nitro group, mediated by trichlorosilane, followed by the addition of an anhydride afforded the corresponding N-aryl carboxyamide, that was isolated after a simple aqueous work up in good-excellent yields. When the methodology was applied to the reaction with γ-butyrolactone, the desired N-aryl butanamide derivative was obtained, featuring a chlorine atom at the γ-position, a functionalized handle that can be used for further synthetic manipulation of the reaction product. Such an intermediate has already been employed as a key advanced precursor of pharmaceutically active compounds.
New synthetic routes for N-substituted 1,n-diamines. II. Synthesis of selectively N-substituted tetra- and pentamethylenediamines from ω-alkanoic acid derivatives
Ramírez, María A.,Corona, María V.,Ortiz, Gisela,Salerno, Alejandra,Perillo, Isabel A.,Blanco, María M.
supporting information; experimental part, p. 1466 - 1468 (2011/06/10)
A new approach for the synthesis of selectively N-substituted tetra- and pentamethylenediamines 1 (n = 4,5) is described. The method uses N-substituted ω-haloalkanamides 2 as precursors and involves the microwave-promoted conversion into ω-azidocarboxamides 3 and later the reduction of both azido and carboxamide groups with diborane.
Reformatsky reactions with N-arylpyrrolidine-2-thiones: Synthesis of tricyclic analogues of quinolone antibacterial agents
Michael, Joseph P,De Koning, Charles B,Hosken, Gladys D,Stanbury, Trevor V
, p. 9635 - 9648 (2007/10/03)
A convenient synthesis of 5-oxo-1,2,3,5-tetrahydropyrrolo[1,2-α]quinoline-4-carboxylic acids, tricylic analogues of the quinolone antibiotics, is described. Key steps in the route are a novel zinc-mediated Reformatsky reaction between diethyl bromomalonate and N-arylpyrrolidine-2-thione 18, and cyclisation of the resulting diethyl pyrrolidinylidenemalonate intermediates 19 in polyphosphoric acid. The products proved to be devoid of biological activity.
Synthesis of 1-[ω-[(arylamino)carbonyl]alkyl]-4-(benzocycloalkyl)piperazines
El-Ahmad, Youssef,Maillet, Philippe,Laurent, Elisabeth,Talab, Akram,Tran, Gilles,Ollivier, Roland
, p. 723 - 734 (2007/10/03)
A series of 1-[co-[(arylamino)carbonyl]alkyl]-4-(benzocycloalkyl)-piperazines (1a-v) was prepared either by reacting the precursor 4-[ω-[(arylamino)carbonyl]alkyl]piperazine (2a-j) with 1-chlorobenzocycloalkanes (3a-c) (Procedure A) or by reacting the N-aryl-ω-chloroalkanamides (5a-j) with the 4-(benzocycloalkyl)piperazines (10a-c) (Procedure B). The best yields were obtained using procedure A.
A versatile synthesis of tricyclic analogues of quinolone antibacterial agents: Use of a novel Reformatsky reaction
Michael, Joseph P.,De Koning, Charles B.,Stanbury, Trevor V.
, p. 9403 - 9406 (2007/10/03)
A simple synthesis of tricyclic analogues of the quinolone antibiotics bearing a diverse range of substituents on the aromatic ring is described. The key steps involve unprecedented Reformatsky reaction between diethyl bromomalonate and N-arylpyrrolidine-2-thiones 8, followed by cyclisation of the resulting enaminone intermediates 9 in polyphosphoric acid.
