N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

• Fatemeh Doraghi,
• Seyedeh Pegah Aledavoud,
• Mehdi Ghanbarlou,
• Bagher Larijani and
• Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

• Nef reaction in MeNO2 under acidic conditions. In the meantime, 1 was activated by AlCl3 to form sulfenium cation I, which induced an intramolecular cyclization of 60 to produce pyrroline 62. In MeCN solvent, 3-thiolated pyrroline 62 was stable and could be isolated, but in MeNO2, in the presence of

Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor

• Dalel El-Marrouki,
• Sabrina Touchet,
• Abderrahmen Abdelli,
• Hédi M’Rabet,
• Mohamed Lotfi Efrit and
• Philippe C. Gros

Beilstein J. Org. Chem. 2020, 16, 1722–1731, doi:10.3762/bjoc.16.144

• the target compounds required the prior preparation of a panel of variously substituted 1,4-diketones 5. The 1,4-diketones 5 have been prepared either by a Nef reaction [56] from the corresponding nitroenone 3 or a Wittig reaction [57] from 1,2-cyclohexanedione and the corresponding ylide 4 (Scheme 2

• reaction, using sodium ethoxide in ethanol, followed by the hydrolysis with concentrated sulfuric acid at a low temperature [56], leading to the corresponding new γ-diketones 5a–d in 61–87% yield (Scheme 2). Despite the efficiency of the Nef reaction, the diversity at the R1 position via this synthetic

• ] derivatives). General strategy to access indole, indolone, and cinnoline derivatives from 1,4-diketones. Synthesis of the 1,4-diketones 5a–k via the Nef reaction or the Wittig reaction. i) HCHO (aq), DMAP, THF, rt, 24 h; ii) Ac2O, Et3N, DMAP, 0 °C, then 2 h, rt; iii) R1–CH2–NO2, Et3N, EtOH, reflux, 24 h; iv

Selected synthetic strategies to cyclophanes

• Sambasivarao Kotha,
• Mukesh E. Shirbhate and
• Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

Cathodic hydrodimerization of nitroolefins

• Michael Weßling and
• Hans J. Schäfer

Beilstein J. Org. Chem. 2015, 11, 1163–1174, doi:10.3762/bjoc.11.131

• the easy access to nitroolefins in large variety, the C–C bond formation with the introduction of two nitro groups in a 1,4-distance and the conversions of the nitro group by reduction to oximes and amines, the conversion into aldehydes and ketones via the Nef reaction and base catalyzed condensations

Simple two-step synthesis of 2,4-disubstituted pyrroles and 3,5-disubstituted pyrrole-2-carbonitriles from enones

• Murat Kucukdisli,
• Dorota Ferenc,
• Marcel Heinz,
• Christine Wiebe and
• Till Opatz

Beilstein J. Org. Chem. 2014, 10, 466–470, doi:10.3762/bjoc.10.44

• the literature. They can be obtained from enones by Michael addition of nitromethane, partial reduction and dehydrogenation of the resulting pyrroline with selenium or sulfur in moderate yields (3 steps) [40][41]. Alternatively, a Nef reaction of the nitromethane adducts gives masked 1,4-dicarbonyls

A versatile and efficient approach for the synthesis of chiral 1,3-nitroamines and 1,3-diamines via conjugate addition to new (S,E)-γ-aminated nitroalkenes derived from L-α-amino acids

• Vera Lúcia Patrocinio Pereira,
• André Luiz da Silva Moura,
• Daniel Pais Pires Vieira,
• Leandro Lara de Carvalho,
• Eliz Regina Bueno Torres and
• Jeronimo da Silva Costa

Beilstein J. Org. Chem. 2013, 9, 832–837, doi:10.3762/bjoc.9.95

• , chiral nitroamines [55][56] are important intermediates directly transformed, via reduction of the nitro group, into diamines [57] or via a Nef reaction in amino acids [58]. Specifically, chiral 1,2-nitroamines have been mainly accessed by direct nucleophilic addition of nitronate anions to imine

A convenient synthesis of γ-functionalized cyclopentenones

• Nour Lahmar,
• Taïcir Ben Ayed,
• Moncef Bellassoued and
• Hassen Amri

Beilstein J. Org. Chem. 2005, 1, No. 11, doi:10.1186/1860-5397-1-11

• 3 in a basic medium, led to the functionalized cyclopentenones 4. Keywords: Nef reaction; conjugated addition; nitroalkanes; 1,4-diketones; functionalized cyclopentenones; Introduction The cyclopentenones are considered as an important class of compounds because they are present in a large variety

• conjugate addition of nitroalkanes to α,β-unsaturated ketones 1 leading to the nitroalkanes derivatives 2 which may be converted into their γ-diketone homologues 3 using Nef reaction. The intramolecular cyclization of 1,4-diketones 3 led to the corresponding cyclopentenones 4. Results and discussion As

•  1). Various synthetic methods were developed to obtain 1,4-diketones [16][17][18][19][20] since these compounds were valuable intermediates in the synthesis of cyclopentenone ring system. Obviously the most straightforward route was the Nef reaction. The transformation of the nitro derivatives to