Tandem Synthesis of Pyrroloacridones via [3 + 2] Alkyne Annulation/Ring-Opening with Concomitant Intramolecular Aldol Condensation

Verma, Akhilesh K.; Kotla, Siva K. Reddy; Aggarwal, Trapti; Kumar, Sonu; Nimesh, Hemlata; Tiwari, Rakesh

doi:10.1021/jo400539x

Cited by 18 publications

(3 citation statements)

References 79 publications

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“…Verma et al reported an efficient Pd-catalyzed cascade synthesis of pyrrolo[3,2,1- d , e ]acridones 130 and 131 from iodopyranoquinolines 127 and symmetrical 128 and unsymmetrical 129 internal alkynes, respectively (Scheme ). Surprisingly, this Pd-catalyzed reaction is a phosphine-free process, which is rare when Pd(OAc) 2 is used as a catalyst. In contrast to the aforementioned reaction with ortho -iodoaniline (Scheme ), unsymmetrical diaryl alkynes 129 reacted with iodopyranoquinolines 127 nonregioselectively, while TMS-(4-tolyl)-acetylene 132 yielded only one regioisomer 133 (for each substrate studied) (Scheme ).…”

Section: Palladium-catalyzed Reactionsmentioning

confidence: 99%

Alkenylation of Arenes and Heteroarenes with Alkynes

et al. 2016

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This review is focused on the analysis of current data on new methods of alkenylation of arenes and heteroarenes with alkynes by transition metal catalyzed reactions, Bronsted/Lewis acid promoted transformations, and others. The synthetic potential, scope, limitations, and mechanistic problems of the alkenylation reactions are discussed. The insertion of an alkenyl group into aromatic and heteroaromatic rings by inter- or intramolecular ways provides a synthetic route to derivatives of styrene, stilbene, chalcone, cinnamic acid, various fused carbo- and heterocycles, etc.

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Section: Palladium-catalyzed Reactionsmentioning

confidence: 99%

Alkenylation of Arenes and Heteroarenes with Alkynes

et al. 2016

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“…A further direction of research was developed in the study of complexes of transition metals, such as Pd [23][24][25], Cu [26][27][28][29][30][31], Cu/Pd [32], Rh [33], Ir [34], Pt [35], Fe/Au [36], Sm [37], Ce [38], etc. They are used as catalysts for the derivation of pyrrolo[1,2-a]quinoline derivatives; however, despite their potential utility, none of these procedures can directly provide end products with a lack of heavy metal admixtures [39][40][41][42].…”

Section: Methodsmentioning

confidence: 99%

Basic approaches to the synthesis of pyrrolo[1,2-a]quinolines derivatives: a review

2019

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At the present stage of the development of organic and bioorganic chemistry, several basic approaches to the synthesis of pyrrolo[1,2-a]quinolines are known. These compounds are of interest to the researches primarily as bioregulators with a wide spectrum of biological activity. This review is an attempt to systematize and generalize literary data relating to the chemistry of pyrrolo[1,2-a]quinoline and its derivatives as important synthetic substrates and precursors for the design of biologically active substances. The main approaches to the synthesis of these compounds, consisting in various preparative methods for constructing a tricyclic base of pyrrolo[1,2-a]quinolone, were considered. The search for biologically active substances of this series is important and has a practical and theoretical significance.

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“…After epoxidation at peripheral positions and convenient derivatization of the epoxides, several stable acridine derivatives can be obtained. These compounds have very promising bioactivities , due to the possibility of intercalation and reversible binding to DNA.…”

Section: Introductionmentioning

confidence: 99%

Biomimetic One-Pot Route to Acridine Epoxides

et al. 2014

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The first direct epoxidation of acridine on the edge positions is reported. The reaction proceeds under mild conditions using a biomimetic catalytic system based on a Mn(III) porphyrin. The successive oxyfunctionalization to mono-, di-, and tetraepoxy derivatives is accomplished using hydrogen peroxide as a green oxidant at room temperature. Computed optimized geometries showed only slight shifts to the base planarity upon dearomatization by epoxidation, which is an important feature for DNA intercalation and bioactivity. NMR studies and comparison with theoretical values allowed the assignment of the stereochemistry of the anti- and syn-diepoxy and -tetraepoxy derivatives as well as compounds resulting from epoxide ring opening, exemplified by epoxydiol. The diepoxide is formed in an anti:syn ratio of ∼4, and the attack by nucleophiles, exemplified by ethylaniline, occurs selectively and with full conversion, using a microwave process with acetonitrile reflux for 10 min. Finally, studies of the electrostatic potential allowed the mechanisms of the formation of 4-hydroxyacridine and the regioselective reaction of diepoxyacridine with nucleophiles to be rationalized.

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Tandem Synthesis of Pyrroloacridones via [3 + 2] Alkyne Annulation/Ring-Opening with Concomitant Intramolecular Aldol Condensation

Cited by 18 publications

References 79 publications

Alkenylation of Arenes and Heteroarenes with Alkynes

Alkenylation of Arenes and Heteroarenes with Alkynes

Basic approaches to the synthesis of pyrrolo[1,2-a]quinolines derivatives: a review

Biomimetic One-Pot Route to Acridine Epoxides

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