2-Iodoisatogens: Versatile Intermediates for the Synthesis of Nitrogen Heterocycles

Maduli, Elvis J. M.; Edeson, Steven J.; Swanson, Stephen; Procopiou, Panayiotis A.; Harrity, Joseph P. A.

doi:10.1021/ol503487f

Cited by 25 publications

(13 citation statements)

References 16 publications

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“…Copper salts proved to be effective to catalyze the cyclization of ortho ‐nitroaryl iodoalkynes for the production of 2‐iodo‐3 H ‐indoles 53 (Scheme 34). [86] The reaction proceeded in the presence of a catalytic amount of copper(I) bromide dimethyl sulfide complex, in THF, and under reflux. This protocol tolerated substrates with more electron‐rich aromatic ring.…”

Section: Synthesis Of 3h‐indolesmentioning

confidence: 99%

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Neto

Zeni

2021

Asian J Org Chem

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This review is intended to highlight the most useful approaches for the synthesis of indole derivatives (azaindoles, carbazoles, carbolines, indazoles, 3H-indoles, indolines, indolizines, isoindoles, and isoindolines), which were described by using transition-metal catalyzed cyclization reactions of alkynes and nitrogen compounds. The methodologies carried out under metal-free conditions will also be illustrated herein. This review will cover the data published mostly in the past decade. Synthesis of 6-AzaindolesAzaindoles, although rare in nature, have attracted a significant attention because some synthetic structures containing this nucleus exhibit biological activities. [17] The synthetic methods describing the preparation of azaindoles are limited. Usually their synthesis was achieved from the cyclization reaction of substrates containing aminopyridines. [18] Transition Metal-Free Synthesis of 6-AzaindolesWe have nominated two methodologies for the preparation of 6-azaindoles, which were developed using alkynes and nitrogen compounds in a metal-free protocol. In the first, an electrophilic cyclization condition, using iodine as an electrophilic source, was applied to 2-(azidomethyl)-3-alkynyl-pyrroles in the preparation of 4-iodo-6-azaindoles 1 (Scheme 1, eq 1). [19] The second approach described the preparation of 2,5-disubstituted 6azaindoles 2 from base-catalyzed intramolecular cyclization of 2-(azidomethyl)-3-alkynyl-pyrroles (Scheme 1, eq 2). [20] 3. Synthesis of 7-Azaindoles Transition Metal-Catalyzed Synthesis of 7-Azaindoles Silver-Catalyzed Synthesis of 7-AzaindolesSilver-catalyzed cyclization reactions of alkynes constitute powerful strategies for the construction of heterocycles. In particular, the 7-azaindoles could be obtained by these approaches. A general method for the preparation of aryl-[a] Dr. J.

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Section: Synthesis Of 3h‐indolesmentioning

confidence: 99%

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Neto

Zeni

2021

Asian J Org Chem

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“…of CuBr.DMS was employed.The utility of these products has been examined by a cross coupling of the iodo at the C2 position with a wide range of alternative heterocyclic derivatives. [13] In 2018, Song and group developed a copper-catalysed cycloisomerization of non-prefunctionalized nitroalkynes 25 for the synthesis of C2-tetrasubstituted indolin-3 ones 28 with BrCF 2 CO 2 R 26 (Scheme 6). In this protocol, diboron acts as the reductant, rendering a fluorine-containing non-carbon quaternary centre in mild to excellent yields.…”

Section: Reported After Yamamoto's 2003 Disclosurementioning

confidence: 99%

Gold‐Catalysed Nitroalkyne Cycloisomerization – Synthetic Utility

Dhote

Halnor

Ramana

2021

The Chemical Record

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“…The method developed by Soderberg consists of catalytic heterocyclization of 1-(2-haloethynyl)-2-nitrobenzenes 33 or 34 and leads to the formation of 2-iodo(bromo)isatogens 35, which further, in refluxing acetone, convert into the corresponding aryl-substituted isatins 2 with moderate to high yields (Scheme 23). 49,50 Ilangovan and co-workers have described an iodination-Kornblum oxidation-nucleophilic addition sequence for the synthesis of diversely substituted isatins 2 from oaminostyrenes 36 or o-aminophenylacetylenes 37 (Scheme 24). 51…”

Section: Miscellaneousmentioning

confidence: 99%

Advances in the Synthesis of Isatins: A Survey of the Last Decade

Богданов

Миронов

2018

Synthesis

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Isatin derivatives are widely used in organic synthesis, in medicinal chemistry and in the chemistry of materials. This report summarizes modern trends in the synthesis of substituted indolin-2,3-diones covering the literature from 2007 to 2017. Studies on the influence of the structure of substituents in the initial substrates on the formation of the heterocyclic isatin system and the yields of the target compounds are also discussed.1 Introduction2 Oxidation of Indole Derivatives3 Cyclization of o-Aminoacetophenones4 Cyclization of N-Acylanilines5 Miscellaneous6 Conclusion

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2-Iodoisatogens: Versatile Intermediates for the Synthesis of Nitrogen Heterocycles

Abstract: A Cu-promoted cyclization of 2-nitrophenyl iodoacetylenes provides a direct route to a range of 2-iodoisatogens. These compounds represent useful intermediates for the late-stage elaboration of the C-I bond to furnish isatins and a range of alternative heterocyclic products.

Cited by 25 publications

References 16 publications

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Gold‐Catalysed Nitroalkyne Cycloisomerization – Synthetic Utility

Advances in the Synthesis of Isatins: A Survey of the Last Decade

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