Copper-mediated oxidative C−H/N−H activations with alkynes by removable hydrazides

• Feng Xiong,
• Bo Li,
• Chenrui Yang,
• Liang Zou,
• Wenbo Ma,
• Linghui Gu,
• Ruhuai Mei and
• Lutz Ackermann

Beilstein J. Org. Chem. 2021, 17, 1591–1599, doi:10.3762/bjoc.17.113

• also proved to be a viable substrate. Thus, the corresponding isoindolone 3aa was assembled via a tandem decarboxylative C−H/C−C sequence (Scheme 3a). The practical relevance of our approach was reflected by the cleavage of the N-2-pyridylhydrazide group, yielding S-3aa (Scheme 3b). Inspired by the

• carboxylate-assisted C−H cleavage to deliver copper(II) intermediate A. Next, the copper(III) carboxylate species B is generated. Thereafter, a facile base-assisted ligand exchange is followed by reductive elimination to afford the alkynylated benzamide D. Finally, the desired isoindolone 3 is formed via an

Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium

• Nadia Bouzayani,
• Jamil Kraїem,
• Sylvain Marque,
• Yakdhane Kacem,
• Abel Carlin-Sinclair,
• Jérôme Marrot and
• Béchir Ben Hassine

Beilstein J. Org. Chem. 2018, 14, 2923–2930, doi:10.3762/bjoc.14.271

• on the 1H-imidazo[2,1-a]isoindolone skeleton, Hosseini-Zare et al. reported the synthesis of new 2,3-diaryl-5H-imidazo[2,1-a]isoindol-5-ones via the one pot reaction of 1,2-diketones, 2-formylbenzoic acid and ammonium acetate [15]. These methodologies usually use toxic solvents such as benzene [16

Organobase-catalyzed three-component reactions for the synthesis of 4H-2-aminopyrans, condensed pyrans and polysubstituted benzenes

• Moustafa Sherief Moustafa,
• Saleh Mohammed Al-Mousawi,
• Maghraby Ali Selim,
• Ahmed Mohamed Mosallam and
• Mohamed Hilmy Elnagdi

Beilstein J. Org. Chem. 2014, 10, 141–149, doi:10.3762/bjoc.10.11

• reacts with DMFDMA to form amidine 38, which undergoes cyclization in refluxing AcOH/NH4OAc to form the 1-amino-pyrrolo[3,4-f]quinazoline 39. We also found that 37a reacts with hydroxylamine hydrochloride in ethanolic sodium acetate solution to form isoindolone derivative 40 (Scheme 11 and Figure 13

The chemistry of isoindole natural products

• Klaus Speck and
• Thomas Magauer

Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243

• ; isoindolinone; isoindolone; natural products; Introduction Isoindole (2H-isoindole, 1), known since more than a century, consists of a fused benzopyrrole ring system and constitutes the regioisomer of the abundant 1H-indole heterocycle. The fully reduced member of the isoindole family is termed isoindoline

• substituted hydroisoindolone moiety fused to a macrocyclic ring (ring size 9–14). In certain cases, the ring system can be oxidized to an unusual cyclic carbonate as observed for cytochalasin E (53). Depending on the amino acid incorporated in the isoindolone moiety, the cytochalasans can be further

Amines as key building blocks in Pd-assisted multicomponent processes

• Didier Bouyssi,
• Nuno Monteiro and
• Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

• . Synthesis of pyrroles by cyclization of propargyl amines. Isoindolone and phthalazone synthesis by cyclization of acylhydrazides. Sultam synthesis by cyclization of sulfonamides. Synthesis of sulfonamides by aminosulfonylation of aryl iodides. Pyrrolidine synthesis by carbopalladation of allylamines