Acetyl Bromide Promoted Sequence <i>via</i> Allene Intermediates: Metal‐Free Construction of 2,3‐Dihydroindenes and Isoindolines

Liu, Le; Yao, Jinzhong; Chen, Dianpeng; Zhou, Hongwei

doi:10.1002/adsc.201600300

Cited by 5 publications

(3 citation statements)

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“…[244] Acetyl bromide promoted metalfree synthesis of isoindolines 172 with high synthetic efficiency via an eneallene as the key intermediary (Table 6, entry 14). [245]…”

Section: Ruthenium-catalyzed Synthesis Of Isoindolinesmentioning

confidence: 99%

“…The reaction involved the simple heating of the reagents in toluene at 90 °C (Table 6, entry 13) [244] . Acetyl bromide promoted metal‐free synthesis of isoindolines 172 with high synthetic efficiency via an eneallene as the key intermediary (Table 6, entry 14) [245] …”

Section: Synthesis Of Isoindolinesmentioning

confidence: 99%

“…[244] Acetyl bromide promoted metalfree synthesis of isoindolines 172 with high synthetic efficiency via an eneallene as the key intermediary (Table 6, entry 14). [245] 12. Summary Over one hundred years studying the indoles delivered to the scientific community impressive advances in biological properties and synthetic applications of these compounds.…”

Section: Transition Metal-free Synthesis Of Isoindolinesmentioning

confidence: 99%

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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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“…[244] Acetyl bromide promoted metalfree synthesis of isoindolines 172 with high synthetic efficiency via an eneallene as the key intermediary (Table 6, entry 14). [245]…”

Section: Ruthenium-catalyzed Synthesis Of Isoindolinesmentioning

confidence: 99%

Section: Synthesis Of Isoindolinesmentioning

confidence: 99%