A Practical Procedure for Preparation ofN-(endo-8-(3-Hydroxy)propyl-8-azabicyclo[3.2.1]oct-3-yl)-1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxamide (TS-951)

New and Expeditious Tandem Sequence Aza-Michael/Intramolecular Nucleophilic Substitution Route to Substituted γ-Lactams: Synthesis of the Tricyclic Core of (±)-Martinellines

“…So, when compound 1j was treated with iron in glacial acetic acid at 80 °C for 3 h, only the iminoamine product 10 was isolated in nearly quantitative yield. 23 This result demonstrated the diastereoselective outcome during the tandem process, i.e., the syn relationship between the aromatic system and the nitrile function to the detriment of the ester group. Following the same protocol, γ-lactam 1k provided the tricyclic lactam 11 in yield of 93%, and its structure was secured by a single X-ray analysis (see Supporting Information for CIF file and ORTEP drawing of product 11).…”

“…In this sense, with both nitrile-ester lactam 1j and diester lactam 1k in hand, two different objectives were pursued: the chemical confirmation of the reaction diastereoselection observed and the synthesis of substituted pyrrolo[3,2- c ]-quinoline 13 as the key for (±)-martinelline alkaloids (Scheme ). So, when compound 1j was treated with iron in glacial acetic acid at 80 °C for 3 h, only the iminoamine product 10 was isolated in nearly quantitative yield . This result demonstrated the diastereoselective outcome during the tandem process, i.e., the syn relationship between the aromatic system and the nitrile function to the detriment of the ester group.…”

Phosphine-Catalyzed [3+2] Cyclizations: Applications to the Enantioselective Synthesis of Cyclopentene-Fused Chromanones and Dihydroquinolinones

“…Substrates 2d-g were prepared according to the literature. 21 Ethyl 1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate (1) was prepared by alkylation of the ethyl 2-oxo-1,2-dihydroquinoline-3-carboxylate 22 with MeI in KOH/EtOH. Substrates 6 23 and 8 24 were prepared according to the literature methods.…”

Convenient variant of the synthesis of 5-oxo-4,5-dihydro-1h-[1,2,3]triazolo[4,5-b]pyridine-6-carboxylic acid

“…Результати досліджень та їх обговорення Нещодавно [16] ми показали, що N-Boc-4-аміно-1,2,3-триазол-5-карбальдегіди 1a-d вступають у конденсацію Фрідлендера із багатьма метиленактивними сполуками (циклоалканони, ацетилацетон, малононітрил) із утворенням карбоанельованих та функціональних похідних [1,2,3]триазоло [4,5-b]піридину. З урахуванням літературних даних щодо синтезу 2-оксохінолін-3-карбонових кислот взаємодією о-амінобензальдегідів із малоновою кислотою [22][23][24] або кислотою Мельдрума [3,25,26]…”