Pyrrolo[1,2-a]quinoxalines from chalcones: An alternate route

Togiti, Uday Kumar; Shukla, A. K.; Bhattacharya, Anupam

doi:10.1016/j.tetlet.2021.153008

Cited by 4 publications

(6 citation statements)

References 27 publications

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“…Yet the examples were limited to intermolecular fashion. In 2021, the group of Bhattacharya developed a rare intramolecular condensation of N ‐(2‐acyl)pyrrolyl nitroarenes [22] . The successive route beginning with t BuOK‐mediated condensation of chalcones and toluenesulfonylmethyl isocyanide (TosMIC) followed by acyl rearrangement and S N Ar reactions afforded the well‐tailored starting materials.…”

Section: Recent Methods For Synthesis Of Pyrrolo/indolo[12‐a]quinoxal...mentioning

confidence: 99%

“…In 2021, the group of Bhattacharya developed a rare intramolecular condensation of N-(2-acyl)pyrrolyl nitroarenes. [22] The successive route beginning with tBuOK-mediated condensation of chalcones and toluenesulfonylmethyl isocyanide (TosMIC) followed by acyl rearrangement and S N Ar reactions afforded the well-tailored starting materials. The ensuing annulation furnished 2,4-diaryl pyrrolo[1,2-a]quinoxalines in moderate yields (up to 66 %).…”

Section: Cyclization Of N-(2-nitroaryl)pyrroles/indolesmentioning

confidence: 99%

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Recent Examples in the Synthesis and Functionalization of C−H Bonds in Pyrrolo/Indolo [1,2‐a]Quinoxalines

Nguyen

2022

ChemistrySelect

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As important molecules that find ubiquitous applications in organic synthesis, medicinal chemistry, and functional materials, pyrrolo/indolo [1,2‐a]quinoxalines have attracted substantial attention. This review features recent development, since 2019, on methods for synthesis of such fused N,N‐heterocycles. In addition, the latest examples related to direct functionalization of C−H bonds in pyrrolo/indolo [1,2‐a]quinoxalines will be discussed as well.

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Section: Recent Methods For Synthesis Of Pyrrolo/indolo[12‐a]quinoxal...mentioning

confidence: 99%

Section: Cyclization Of N-(2-nitroaryl)pyrroles/indolesmentioning

confidence: 99%

Recent Examples in the Synthesis and Functionalization of C−H Bonds in Pyrrolo/Indolo [1,2‐a]Quinoxalines

Nguyen

2022

ChemistrySelect

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“…Amount of starting material: 3 g; amount of 2p: 1.87 g; isolated yield: 55% as colourless viscose 3.81 (s, 3H, -OCH3), 2.96 (dt, J=2.5, 6.9 Hz, 2H, -CH2), 1.96 (q, J=2.5 Hz, 1H, -CH). 13 C-NMR (CDCl3,100 MHz):193.0,164.0,131.1,129.1,128.8,114.1,113.9,81.4,70.7,55.5,55.2,19. 9,193.1,139.1,164.0,157.5,133.1,131.3,130.3,128.7,125.8,114.1,113.8,81.3,70.7,55.5,55.4,35.2,30.9,191. HRMS Anal.Calcd. for C23H24O3 [M + H]: 349.17982, Found 349.18018.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…13 C-NMR (CDCl3, 100 MHz): δ 164. 9,143.6,131.6,130.5,130.2,129.6,127.6,127.2,123.5,118.1,115.6,109.1,59.4,14.2,12.1. HRMS Anal.Calcd. for C20H20N2O2…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…Some publications indicated the use of transition metals, and others discussed metal-free reaction conditions (Scheme 1, reaction a). [4][5][6][7][8][9][10] According to the literature, the same procedures utilized in synthesizing 5x limit the pyrrole ring derivatization. Thus, new approaches for determining distinct functional groups in the 5y and quinoxaline skeletons could significantly contribute to the literature.…”

Section: Introductionmentioning

confidence: 99%

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A Golden Synthetic Approach to 2-(1H-Pyrrol-1-yl)anilines and Pyrrolo[1,2-a]quinoxalines through a Gold Carbene Intermediate

Menges,

Tasdemir,

Genç

2023

Synlett

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The pyrrolo[1,2-a]quinoxaline skeleton has significant potential for many biological and optical applications. Hence, in this study, unconjugated ynone derivatives are reacted with 1,2-diaminoarenes under gold-catalyzed cyclization. The reaction gives 2(1H-pyrrole-1yl)-aniline, which is a valuable starting material, and Pyrrolo[1,2-a]quinoxaline through a one-pot and single-step approach. A reaction mechanism for the formation of the pyrrolo[1,2-a]quinoxaline skeleton featuring a key gold-carbene intermediate is proposed. On the other hand, the methyl group on the C-2 position of 2(1H-pyrrole-1yl)-anilines is oxidized with SeO2, resulting in a pyrrolo[1,2-a]quinoxaline skeleton, which gives 14 different pyrrolo[1,2-a]quinoxaline derivatives.

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Mo–Catalyzed One‐Pot Synthesis of N‐Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent‐Tuned Photophysical Properties

Hernández-Ruiz

Rubio-Presa

Suárez‐Pantiga

et al. 2021

Chemistry A European J

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A catalytic domino reduction–imine formation–intramolecular cyclization–oxidation for the general synthesis of a wide variety of biologically relevant N‐polyheterocycles, such as quinoxaline‐ and quinoline‐fused derivatives, and phenanthridines, is reported. A simple, easily available, and environmentally friendly dioxomolybdenum(VI) complex has proven to be a highly efficient and versatile catalyst for transforming a broad range of starting nitroarenes involving several redox processes. Not only is this a sustainable, step‐economical as well as air‐ and moisture‐tolerant method, but also it is worth highlighting that the waste byproduct generated in the first step of the sequence is recycled and incorporated in the final target molecule, improving the overall synthetic efficiency. Moreover, selected indoloquinoxalines have been photophysically characterized in cyclohexane and toluene with exceptional fluorescence quantum yields above 0.7 for the alkyl derivatives.

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Pyrrolo[1,2-a]quinoxalines from chalcones: An alternate route

Cited by 4 publications

References 27 publications

Recent Examples in the Synthesis and Functionalization of C−H Bonds in Pyrrolo/Indolo [1,2‐a]Quinoxalines

Recent Examples in the Synthesis and Functionalization of C−H Bonds in Pyrrolo/Indolo [1,2‐a]Quinoxalines

A Golden Synthetic Approach to 2-(1H-Pyrrol-1-yl)anilines and Pyrrolo[1,2-a]quinoxalines through a Gold Carbene Intermediate

Mo–Catalyzed One‐Pot Synthesis of N‐Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent‐Tuned Photophysical Properties

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