A microwave-assisted intramolecular aminopalladation-triggered domino sequence: an atom economical route to 5,10-dihydroindeno[1,2-<i>b</i>]indoles

Jandial, Tanvi; Gupta, Anish; Jan, Gowsia; Karuppasamy, Muthu; Nagarajan, Subbiah; Maheswari, Uma; Sridharan, Vellaisamy

doi:10.1039/d3ob00041a

Cited by 5 publications

(3 citation statements)

References 55 publications

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“…Full experimental details, complete characterization data, single-crystal X-ray data of 2a, 4, 5a and copies of NMR spectra (PDF) FAIR data, including the primary NMR FID files, for compounds 1c 2w',3,4,[6][7][8][9][10][11][12]…”

Section: Data Availability Statementmentioning

confidence: 99%

“…5 Of late, Sridharan and co-workers revealed a Pd-catalyzed and microwaveassisted method for the synthesis of DHIIs. 6 Nonetheless, few other metal-catalyzed protocols offering DHII derivatives in a stepwise manner are documented in the literature. 7 However, we strongly believe that there is a need to set up a straightforward, mild, and modular pathway for the synthesis of DHIIs which have been used as a key starting material (KSM) in bioorthogonal chemistry.…”

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confidence: 99%

“…However, the most useful and common pathway to construct DHIIs is Fisher-indole synthesis between phenyl hydrazine and 1-indanone under strong acidic conditions . Of late, Sridharan and co-workers revealed a Pd-catalyzed and microwave-assisted method for the synthesis of DHIIs . Nonetheless, few other metal-catalyzed protocols offering DHII derivatives in a stepwise manner are documented in the literature .…”

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confidence: 99%

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p-TsOH-Mediated Intramolecular C2-Arylation on NH-Indoles: Access of 5,10-Dihydroindeno[1,2-b]indoles

Verma,

Kant,

Ghosh

2024

Org. Lett.

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5,indole has served as an important starting precursor for BARAC-fluor reagent in medicinal chemistry. Herein, an unprecedented p-TsOH assisted intramolecular C2-arylation of NH-indoles via C(sp 2 )-CN/C(sp 2 )-H coupling, offering a series of 5,10-dihydroindeno[1,2-b]indoles with moderate to good yields, has been showcased under redox-neutral conditions. Furthermore, successful scalability and synthetic applications highlight the practical nature of the method.

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confidence: 99%

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confidence: 99%

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p-TsOH-Mediated Intramolecular C2-Arylation on NH-Indoles: Access of 5,10-Dihydroindeno[1,2-b]indoles

Verma,

Kant,

Ghosh

2024

Org. Lett.

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Rapid Assembly of Functionalized 2H-Chromenes and 1,2-Dihydroquinolines via Microwave-Assisted Secondary Amine-Catalyzed Cascade Annulation of 2-O/N-Propargylarylaldehydes with 2,6-Dialkylphenols

Rajput,

Jan,

Karuppasamy

et al. 2023

J. Org. Chem.

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An efficient, secondary amine-catalyzed cascade annulation of 2-O/N-propargylarylaldehydes with 2,6-dialkylphenols was established to access biologically relevant functionalized 2H-chromenes and 1,2-dihydroquinolines tethered with a synthetically useful p-quinone methide scaffold in high yields under microwave irradiation and conventional heating conditions. The microwave-assisted strategy was convenient, clean, rapid, and high yielding in which the reactions were completed in just 15 min, and the yields obtained were up to 95%. This highly atom-economical domino process constructed two new C–C double bonds and a six-membered O/N-heterocyclic ring in a single synthetic operation. Its mechanism process was rationalized as involving sequential iminium ion formation, nucleophilic addition, and intramolecular annulation steps. Furthermore, the synthesized 2H-chromene derivatives were transformed into valuable indeno[2,1-c]chromenes, 5H-indeno[2,1-c]quinolines, and oxireno[2,3-c]chromene via a palladium-catalyzed double C–H bond activation process and epoxidation, respectively.

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Microwave-Assisted Selective Nucleopalladation-Triggered Cascade Process: Synthesis of Highly Functionalized 3-Chloro-1H-indenes

Jandial,

Gupta,

Tsering

et al. 2024

J. Org. Chem.

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A nucleopalladation-triggered cascade transformation of internal alkynes bearing an amino nucleophile and an electrophilic enone was investigated under unconventional microwave-assisted conditions. Among the three possible pathways, the chloropalladation-triggered domino process proceeded selectively to furnish 3-chloro-1H-indenes in good to excellent yields. The reactions under microwave irradiation were completed in 30 min, and the conventional heating required 3−5 h for completion. The yields obtained under nonclassical heating using microwave irradiation are marginally higher (71−97%) than those of the conventional heating conditions (67−96%). The mechanism of this domino process involves chloropalladation of alkynes to deliver σ-vinylpalladium intermediates, intramolecular carbopalladation via Heck-type olefin insertion, and protodepalladation steps. The other two competitive intramolecular aminopalladation-initiated cascades via 7-endo-dig or 6-exo-dig cyclizations leading to oxazepine or benzoxazine scaffolds were not observed.

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A microwave-assisted intramolecular aminopalladation-triggered domino sequence: an atom economical route to 5,10-dihydroindeno[1,2-b]indoles

Abstract: A microwave-assisted, palladium(II)-catalyzed cascade reaction of 2-alkynylanilines tethered with α,β-unsaturated carbonyl moiety was established to access 5,10-dihydroindeno[1,2-b]indoles in high yields (up to 84%) in a short reaction time. This operationally...

Cited by 5 publications

References 55 publications

p-TsOH-Mediated Intramolecular C2-Arylation on NH-Indoles: Access of 5,10-Dihydroindeno[1,2-b]indoles

p-TsOH-Mediated Intramolecular C2-Arylation on NH-Indoles: Access of 5,10-Dihydroindeno[1,2-b]indoles

Rapid Assembly of Functionalized 2H-Chromenes and 1,2-Dihydroquinolines via Microwave-Assisted Secondary Amine-Catalyzed Cascade Annulation of 2-O/N-Propargylarylaldehydes with 2,6-Dialkylphenols

Microwave-Assisted Selective Nucleopalladation-Triggered Cascade Process: Synthesis of Highly Functionalized 3-Chloro-1H-indenes

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