A rhodium(<scp>ii</scp>) catalysed domino synthesis of azepino fused diindoles from isatin tethered<i>N</i>-sulfonyl-1,2,3-triazoles and indoles

Kahar, Nilesh M.; Jadhav, Pankaj Pandit; Reddy, R. V. Ramana; Dawande, Sudam Ganpat

doi:10.1039/c9cc08377d

Cited by 16 publications

(5 citation statements)

References 86 publications

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“…Yield of 490 mg (1.60 mmol, 80%). 1 10): This method was developed in analogy to that described in the literature [41]. To the solution of (E)-2-methyl-3-(2-nitrovinyl)-1H-indole (10aa) (202 mg, 2.00 mmol) in DMF (2 mL), NaH (120 mg, 3.00 mmol, 60% in mineral oil) was added portionwise at 0 • C; then, the mixture was stirred for 30 min.…”

Section: Synthesis Of Starting 1h-indole-3-carbaldehydes (29)mentioning

confidence: 99%

“…Yield of 237 mg (0.81.00 mmol, 81%). 1 H NMR (400 MHz, CDCl 3 ) δ 8.39 (d, J = 13.3 Hz, 1H), 7.84 (d, J = 13.2 Hz, 1H), 7.79-7.74 (m, 1H), 7.33-7.27 (m, 6H), 7.00 (dd, J = 7.6, 1.9 Hz, 2H), 5.39 (s, 2H), 2.55 (s, 3H); 13 10): This method was developed in analogy to that described in the literature [41]. To the solution of (E)-2-methyl-3-(2nitrovinyl)-1H-indole (10aa) (202 mg, 2.00 mmol) in DMF (2 mL), NaH (120 mg, 3.00 mmol, 60% in mineral oil) was added portionwise at 0 ℃; then, the mixture was stirred for 30 min.…”

Section: Synthesis Of Starting 1h-indole-3-carbaldehydes (29)mentioning

confidence: 99%

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Synthesis of β-Carbolines with Electrocyclic Cyclization of 3-Nitrovinylindoles

Aksenov,

Arutiunov,

Aksenov

et al. 2023

IJMS

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The β-carboline motif is common in drug discovery and among numerous biologically active natural products. However, its synthetic preparation relies on multistep sequences and heavily depends on the type of substitution required in the core of the desired β-carboline target. Herein, we demonstrate that this structural motif can be accessed with the microwave-assisted electrocyclic cyclization of heterotrienic aci (alkylideneazinic acid) forms of 3-nitrovinylindoles. The reaction can start with 3-nitrovinylindoles themselves under two sets of conditions. The first one involves microwave irradiation of butanolic solutions of 3-nitrovinylindoles, whereas the second one consists of prior Boc protection of indolic nitrogen, where the protecting group cleanly comes off during the course of the reaction. Alternatively, the reaction can start with 3-nitrovinylindoles prepared in situ using various processes. Finally, the reaction may utilize indoles with β-nitrostyrenes, likely involving the intermediacy of spirocyclic oxazolines, which rearrange to similar heterotrienic systems undergoing cyclization to β-carbolines. As part of this study, several natural products, namely, alkaloids norharmane, harmane, and eudistomin N, were synthesized.

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Section: Synthesis Of Starting 1h-indole-3-carbaldehydes (29)mentioning

confidence: 99%

Section: Synthesis Of Starting 1h-indole-3-carbaldehydes (29)mentioning

confidence: 99%

Synthesis of β-Carbolines with Electrocyclic Cyclization of 3-Nitrovinylindoles

Aksenov,

Arutiunov,

Aksenov

et al. 2023

IJMS

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“…Very recently, Dawande and co-workers developed a Rh-catalyzed domino synthesis of azepino-fused diindoles 193.3 from isatin-tethered 1,2,3-triazoles 193.1 and indoles 193.2 (Scheme ). Various diindoles were synthesized in good to high yields.…”

Section: Denitrogenative Transformations Of Triazolesmentioning

confidence: 99%

“…Very recently, Dawande and co-workers 286 194). The readily available complex Cu(Ph 3 P) 3 Br was found to be the optimal catalyst, providing the highest yields with trace amounts of byproduct formation.…”

Section: Miscellaneousmentioning

confidence: 99%

1,2,3-Triazole and Its Analogues: New Surrogates for Diazo Compounds

2022

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Readily accessible and shelf-stable 1,2,3-triazole and its analogues such as pyridotriazole, triazoloindole, benzotriazole, and thiadiazole exist in equilibrium with their ring-opened isomers, viz., diazo compounds. These ring-opened isomers could be trapped by various metal catalysts (e.g., Rh, Pd, Cu, Co, Ag, etc.) to generate the corresponding metal carbenoids with extrusion of nitrogen. As a consequence, these unique N-heterocycles facilitate access to a realm of N-containing complex structural motifs of biological importance through denitrogenative transformations such as transannulations, insertions, ylide formation, and rearrangements by trapping of the metal carbenoids with a diverse range of coupling partners (e.g., alkenes, alkynes, nitriles, carbo/heterocycles, X–H/C–X bonds, etc.). Hence, suitably substituted triazole derivatives have emerged as efficient surrogates of diazo compounds for the generation of reactive metal carbenoids during the past decades. In this comprehensive review, we aim to discuss in detail the remarkable advancement in their synthesis and synthetic applications.

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“…The reactivity of these carbene intermediates has been significantly explored to achieve the synthesis of organic molecules of interest. 17,18 With competent reaction partners, N-sulfonyl-1,2,3-triazoles offer reactions such as transannulation, cycloaddition, X-H insertion, migratory insertion to (hetero)arenes, and cascade reactions through an oxonium ylide intermediate. Furthermore, the generated α-imino rhodium(II) carbenoids are known to undergo carbonyl oxygen insertion and subsequent rearrangement.…”

mentioning

confidence: 99%