Sulfanyl-methylene-5(4H)-oxazolones and β-sulfanyl-α-nitroacrylates as appealing dienophiles for the synthesis of conformationally constrained cysteine analogues

Identification of the first enantiopure Rac1–Tiam1 protein–protein interaction inhibitor and its optimized synthesis via phosphine free remote group directed hydroarylation

“…Our previous studies 14,25 disclosed that the regioselectivity is mainly driven by a long range effect exerted by the nitro group on C-2, (Path a, Fig. 3).…”

Trisubstituted push-pull nitro alkenes

“…The first method A (Scheme 1) is the most exploited preparation of reviewed structures of nitroenolethers where ether alkyl is mostly lower alkyl (methyl, ethyl). 12,16,17,19,[25][26][27][28][29][30][31][32] The reaction of ethyl orthoformate and acetic anhydride with active methylene compounds was reported by Claisen 33 in 1893. The modification 28 for alkyl nitroacetates was first time reported in 1959.…”

“…The value of this group of compounds can be demonstrated by their utilization as a reagent in the synthesis of biologically active compounds over the years. [14][15][16][17][18][19][20] For instance, they have been used in rational drug design of topically administered caspase 1 inhibitors for the treatment of inflammatory acne, 14 in the synthesis and biological evaluation of pyrimidine derivatives as novel human Pin1 inhibitors in the cancer treatment, 15 and the preparation of scaffolds for the design of Rac1−Tiam1 protein−protein interaction inhibitors 16,17 . Title compounds were also employed in the synthesis of alkaloid meridianin G, 18 and the synthesis of the insect feeding deterrent peramine.…”

Synthesis of α-Amino Esters via α-Nitro or α-Oxime Esters: A Review

“…29a,121 Subsequent reports confirmed the potential of 3-ethoxy-2-nitroacrylate 74 as a building block in the preparation of tryptophan 122 or pyrrole 123 derivatives as well as constrained cysteines. 124 However, a completely unexpected side reaction was reported when imidazole and 3-ethoxy-2-nitroacrylate 74 were stirred in acetonitrile. 125 The nitronate salt 78, obtained by a basic treatment of 2-nitroacrylate 77, 100h initially gave access to dehydrovaline ester 79 via a reduction using tin and hydrochloric acid.…”