Metal-free, visible-light-promoted oxidative radical cyclization of <i>N</i>-biarylglycine esters: one-pot construction of phenanthridine-6-carboxylates in water

Natarajan, Palani; Chuskit, Deachen; Priya, .

doi:10.1039/c9gc01557d

Cited by 34 publications

(23 citation statements)

References 56 publications

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“…According to our mechanistic findings and literature precedents, 21 the tentative reaction pathway for assembling the two classes of phenanthridines by divergent [5 + 1] annulation is proposed ( Scheme 7 ). Under acidic conditions, the protonation of a diazo compound initially takes place to deliver species A , followed by N 2 extrusion 21 a – c to produce secondary amine B via nucleophilic attack of NH 2.…”

Section: Resultsmentioning

confidence: 79%

Metal-free tandem carbene N–H insertions and C–C bond cleavages

Chen

Jiang

et al. 2021

Chem. Sci.

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Section: Resultsmentioning

confidence: 79%

Metal-free tandem carbene N–H insertions and C–C bond cleavages

Chen

Jiang

et al. 2021

Chem. Sci.

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“…Natarajan and co‐workers in 2019 developed a metal‐free, novel, efficient, atom economical, and eco‐friendly synthetic protocol of phenanthridine‐6‐carboxylates 319 from N ‐biarylglycine esters 318 under the assistance of rose bengal which acts as a photocatalyst [94] . This reaction is carried out through the irradiation of blue LED in presence of water as solvent and molecular oxygen as oxidant.…”

Section: Synthesis Of Phenanthridinesmentioning

confidence: 99%

“…Natarajan and co-workers in 2019 developed a metal-free, novel, efficient, atom economical, and ecofriendly synthetic protocol of phenanthridine-6-carboxylates 319 from N-biarylglycine esters 318 under the assistance of rose bengal which acts as a photocatalyst. [94] This reaction is carried out through the irradiation of blue LED in presence of water as solvent and molecular oxygen as oxidant. A radical intermediate is generated from N-biarylglycine esters 318 which takes part in intramolecular cyclization reaction followed by dehydrogenation in one-pot to form phenanthridine derivatives in excellent yields (Scheme 111).…”

Section: Radical-mediated Cyclization Reactionsmentioning

confidence: 99%

Recent Trends in the Synthesis and Mechanistic Implications of Phenanthridines

et al. 2021

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Phenanthridine derivatives are one of the most intensively studied families of biologically active compounds. There has been considerable scientific interest in the turn of this century in the synthesis of these N‐containing heterocycles as they are prevalent in many alkaloids and also possess striking biological activities including antibacterial, antifungal, antitumor activities. In this regard, a number of synthetic approaches toward the construction of phenanthridine moieties with various substituents, and to increase their yield have been developed by the synthetic organic community. Even though many researchers have developed various innovative methods for the synthesis of phenanthridine derivatives for the past few years, still there is substantial scope for the discovery of novel synthetic methods. In this review, the latest developments in the diverse synthetic strategies of phenanthridine derivatives in the presence and absence of metals were described. The present review also enlightens the use of different reagents, the diversity of the substrates identified, and the plausible mechanisms unravelled towards the construction of these biologically relevant scaffolds.

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“…A complementary approach in the synthesis of 6-arylphenanthridines started from N-(2-aminoaryl)benzoimine 11.1 and involved the formation of a C(sp 2 )-C(sp 2 ) bond via an aryl desired phenanthridines, which could be isolated in a pure form by a simple filtration [74].…”

Section: Synthesis Of Phenanthridines Via Photocatalyzed Intramoleculmentioning

confidence: 99%