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

• -pyridylhydrazide allowed for domino C–H/N–H functionalization. The approach featured remarkable functional group compatibility and ample substrate scope. Thereby, highly functionalized aromatic and heteroaromatic isoindolin-1-ones were accessed with high efficacy with rate-limiting C–H cleavage. Keywords

Atom-economical group-transfer reactions with hypervalent iodine compounds

• Andreas Boelke,
• Peter Finkbeiner and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2018, 14, 1263–1280, doi:10.3762/bjoc.14.108

• [31]. Under copper-catalysis diarylated isoindolin-1-ones 9 were formed starting from 2-formylbenzonitriles 8 upon treatment with mesityl(aryl)iodonium salts 1a (Scheme 6). A plausible reaction mechanism starts with the selective terminal arylation of the nitrile, forming the arylnitrilium cation A

• dithiocarbamates 7 and 7’ from one equivalent of diaryliodonium salt 1. Synthesis of substituted isoindolin-1-ones 9 from 2-formylbenzonitrile 8 and the postulated reaction mechanism. Domino C-/N-arylation of indoles 10. Domino modification of N-heterocycles 12 via in situ-generated directing groups. Synthesis of

The photodecarboxylative addition of carboxylates to phthalimides as a key-step in the synthesis of biologically active 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones

• Ommid Anamimoghadam,
• Saira Mumtaz,
• Anke Nietsch,
• Gaetano Saya,
• Cherie A. Motti,
• Jun Wang,
• Peter C. Junk,
• Ashfaq Mahmood Qureshi and
• Michael Oelgemöller

Beilstein J. Org. Chem. 2017, 13, 2833–2841, doi:10.3762/bjoc.13.275

• 9, Ireland Australian Institute of Marine Science, Townsville, Queensland, Australia Bahauddin Zakariya University, Institute of Chemical Sciences, Multan, Pakistan 10.3762/bjoc.13.275 Abstract The synthesis of various 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones was realized following a simple

• -dihydro-1H-isoindolin-1-ones via acid-catalyzed dehydration and subsequent nucleophilic substitution with the corresponding secondary amines. The procedure was successfully applied to the synthesis of known local anesthetics (AL-12, AL-12B and AL-5) in their neutral forms. Keywords: anesthetics

• ; arylmethylenedihydroisoindolinones; photochemistry; photodecarboxylation; phthalimide; Introduction Phthalimides and their related 3-alkyl- and 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones play an important role in medicinal chemistry due to their biological activities for a wide range of therapeutic applications [1][2][3][4

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

• Mohammad Haji

Beilstein J. Org. Chem. 2016, 12, 1269–1301, doi:10.3762/bjoc.12.121

• dephosphorylated by treatment with lithium aluminum hydride to give isoindolin-1-ones 61 (Scheme 15). Also the Kabachnik–Fields reaction of formylbenzoic acid (55), dimethyl phosphonate and amines 62 or 66 followed by subsequent Horner–Wadsworth–Emmons reaction of the resulting cycloadducts 63 and 67 with

• isoindolin-1-one-3-phosphonates. A microwave-assisted Kabachnik–Fields reaction toward isoindolin-1-ones. The synthesis of 3-arylmethyleneisoindolin-1-ones through a Horner–Wadsworth–Emmons reaction of Kabachnik–Fields reaction products. An efficient one-pot method for the synthesis of ethyl (2-alkyl- and 2

Aza-Diels–Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome

• Amitabh Jha,
• Ting-Yi Chou,
• Zainab ALJaroudi,
• Bobby D. Ellis and
• T. Stanley Cameron

Beilstein J. Org. Chem. 2014, 10, 848–857, doi:10.3762/bjoc.10.81

• expected based on literature reports [11][12][13][14][15][16][17]. The unpredicted formation of E-2-(2-substituted-aryl)-3-(2-(2-oxopyrrolidin-1-yl)vinyl)isoindolin-1-ones (series 3, Figure 1) from N-(2-substituted-aryl)-1-oxo-1H-isoindolium ions (A) and tert-enamides under identical conditions forms the

• the same fate of condensation without further electrophilic aromatic substitution. Lu et al. [43] have recently reported the synthesis of 3-(1-alkenyl)isoindolin-1-ones from N-acyliminium cations; however, their intermediates did not have the opportunity for intramolecular cyclization. The nitrogen

• -dihydroisoindolo[2,1-a]quinolin-11(5H)-ones (1a–h); 5-(2-oxoazepan-1-yl)-6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)-ones (2a–h) and (E)-2-(2-substitued-phenyl)-3-(2-(2-oxopyrrolidin-1-yl)vinyl)isoindolin-1-ones (3a–i) Appropriate N-aryl-3-hydroxyisoindolinones (500 mg) from the previous step were dissolved in

Synthesis of conformationally restricted glutamate and glutamine derivatives from carbonylation of orthopalladated phenylglycine derivatives

• Esteban P. Urriolabeitia,
• Eduardo Laga and
• Carlos Cativiela

Beilstein J. Org. Chem. 2012, 8, 1569–1575, doi:10.3762/bjoc.8.179

• functional groups on the same starting material (methyl phenylglycinate) are changed. In particular, we have detected that the presence of different types of substituents at the nitrogen atom has a critical effect on the final outcome of the reaction and that, instead of the expected (1H)-isoindolin-1-ones

A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins

• Nianhong Lu,
• Lihong Wang,
• Zhanshan Li and
• Wei Zhang

Beilstein J. Org. Chem. 2012, 8, 192–200, doi:10.3762/bjoc.8.21

• Nianhong Lu Lihong Wang Zhanshan Li Wei Zhang State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China; Fax: +86 (931) 8625657 10.3762/bjoc.8.21 Abstract A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones has been achieved by

• -alkenylboronates with 2-ethoxy-N-acylquinolines catalyzed by tartaric acid to produce 2-(1-alkenyl)-N-acylquinolines in 2011 [23]. We report here a concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the cross-coupling reactions of N-acyliminium ions derived from 3-hydroxyisoindol

• results of our investigation have furnished another route to the synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones. Results and Discussion Two kinds of N-acyliminium ion precursors, 3-hydroxyisoindol-1-ones (1a–c) and 5-hydroxypyrrol-2-ones (5a,b) were easily prepared by the

A simple and convenient one-pot synthesis of substituted isoindolin-1-ones via lithiation, substitution and cyclization of N'-benzyl-N,N-dimethylureas

• Keith Smith,
• Gamal A. El-Hiti,
• Amany S. Hegazy and
• Benson Kariuki

Beilstein J. Org. Chem. 2011, 7, 1219–1227, doi:10.3762/bjoc.7.142

• 10.3762/bjoc.7.142 Abstract Lithiation of N'-benzyl-N,N-dimethylurea and its substituted derivatives with t-BuLi (3.3 equiv) in anhydrous THF at 0 °C followed by reaction with various electrophiles afforded a range of 3-substituted isoindolin-1-ones in high yields. Keywords: N'-benzyl-N,N-dimethylureas

• ; isoindolin-1-ones; directed lithiation; electrophiles; substitution; synthesis; Introduction In recent years there has been a great deal of interest in compounds possessing an isoindolinone ring system since it represents the core unit of numerous naturally occurring substances [1][2][3][4][5][6][7][8

• approaches to the synthesis of isoindolin-1-ones have been reported (Scheme 1 and Scheme 2) [43][45]. One method simply involves lithiation of a preformed isoindolin-1-one ring system at the 3-position followed by treatment with an electrophile (Scheme 1) [43]. While this approach is straightforward, clearly