NH2SO3H and H6P2W18O62 · 18H2O-Catalyzed, Three-Component, One-Pot Synthesis of Benzo[c]acridine Derivatives

Heravi, Majid M.; Alinejhad, Hamideh; Derikvand, Fatemeh; Oskooie, Hossein A.; Baghernejad, Bita; Bamoharram, Fatemeh F.

doi:10.1080/00397911.2010.550704

Cited by 10 publications

(3 citation statements)

References 17 publications

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“…On the other hand, as specific aromatic amines, the more nucleophilic 𝛼and 𝛽-naphthylamines with fixed ortho-nucleophilic-site have been used as 1,3-binucleophiles for few enantioselective cyclization reactions. [17,18] We report herein the successful realization of this endeavor via chiral phosphoric acid catalyzed CACR of diverse anilines and vicinal diketones using a simple procedure, which provides a modular and general synthesis of 2,2-disubstituted indolin-3-ones in a high level of yield and enantiopurity (Scheme 1D). Mechanistic studies as well as further synthetic transformations of the resulting products were also performed.…”

Section: Doi: 101002/advs202402532mentioning

confidence: 99%

Catalytic Asymmetric Cyclizative Rearrangement of Anilines and Vicinal Diketones to Access 2,2‐Disubstituted Indolin‐3‐ones

Quan,

Li,

Wang

et al. 2024

Advanced Science

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The efficient synthesis of chiral 2,2‐disubstituted indolin‐3‐ones is of great importance due to its significant synthetic and biological applications. However, catalytic enantioselective methods for de novo synthesis of such heterocycles remain scarce. Herein, a novel cyclizative rearrangement of readily available anilines and vicinal diketones for the one‐step construction of enantioenriched 2,2‐disubstituted indolin‐3‐ones is presented. The reaction proceeds through a self‐sorted [3+2] heteroannulation/regioselective dehydration/1,2‐ester shift process. Only chiral phosphoric acid is employed to promote the entire sequence and simplify the manipulation of this protocol. Various common aniline derivatives are successfully applied to asymmetric synthesis as 1,3‐binuclephiles for the first time. Remarkably, the observed stereoselectivity is proposed to originate from an amine‐directed regio‐ and enantioselective ortho‐Csp2‐H addition of the anilines to the ketones. A range of synthetic transformations of the resulting products are demonstrated as well.

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Section: Doi: 101002/advs202402532mentioning

confidence: 99%

Catalytic Asymmetric Cyclizative Rearrangement of Anilines and Vicinal Diketones to Access 2,2‐Disubstituted Indolin‐3‐ones

Quan,

Li,

Wang

et al. 2024

Advanced Science

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“…However, in spite of many advantages of these methods, they also have their limitations such as low yield and prolonged reaction time. More recently, these N ‐heterocycles are also prepared by recyclable catalyst i.e γ‐Fe 2 O 3 @Si‐(CH 2 ) 3 @mel@(CH 2 ) 4 SO 3 H nanocatalyst, [74] L ‐proline, [75] NH 2 SO 3 H & H 6 P 2 W 18 O 62 .18H 2 O [76] . Moreover, benzoacridinones derivatives are also synthesized by combinatorial synthesis from aldehyde, amine, and cyclohexan‐1,3‐diones without using any catalyst [77] …”

Section: Introductionmentioning

confidence: 99%

“…More recently, these N-heterocycles are also prepared by recyclable catalyst i.e γ-Fe 2 O 3 @Si-(CH 2 ) 3 @mel@(CH 2 ) 4 SO 3 H nanocatalyst, [74] L-proline, [75] NH 2 SO 3 H & H 6 P 2 W 18 O 62 .18H 2 O. [76] Moreover, benzoacridinones derivatives are also synthesized by combinatorial synthesis from aldehyde, amine, and cyclohexan-1,3-diones without using any catalyst. [77] Additionally, pyridine derivatives made up from cyclohexan-1,3-diones are another class of biologically active sixmembered N-heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

Sharma¹,

Kumar

et al. 2022

ChemistrySelect

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Cyclohexane‐1,3‐dione and its derivatives are imperative precursors in synthetic organic chemistry as they are useful intermediates for the synthesis of a wide range of biologically active natural products, heterocycles and pharmaceuticals. Recently, cyclohexane‐1,3‐diones have been used for the synthesis of varied array of six‐membered nitrogen‐containing heterocycles in the presence of aldehydes, acetoacetic esters, malononitrile, chalcones, coumarins, acetophenones, amino acids, amines, etc. under catalytic and non‐catalytic conditions. Newest studies on the importance of these heterocycles motivated us to compile all the recently developed processes which include the fabrication of six‐membered nitrogen heterocycles. This article is mainly focused on the efficient synthesis of six‐membered N‐heterocycles i. e. 1,4‐dihydropyridine, acridine‐1,8‐diones, benzoacridinones, quinolones and pyridine derivatives from cyclohexane‐1,3‐diones as one of the substrates, published for the last ten years.

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ChemInform Abstract: NH₂SO₃H and H₆P₂W₁₈O₆₂·18H₂O‐Catalyzed, Three‐Component, One‐Pot Synthesis of Benzo[c]acridine Derivatives.

Heravi¹,

Alinejhad²,

Derikvand³

et al. 2012

ChemInform

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Catalyzed, Three-Component, One-Pot Synthesis of Benzo[c]acridine Derivatives. -An efficient and practical three-component, one-pot preparation of polyhydroacridine derivatives proceeds under neat conditions in the presence of sulfamic acid or Wells-Dawson acid as catalyst. -(HERAVI*, M. M.; ALINEJHAD, H.; DERIKVAND, F.; OSKOOIE, H. A.; BAGHERNEJAD, B.; BAMOHARRAM, F. F.; Synth. Commun. 42 (2012) 14, 2033-2039, http://dx.

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NH₂SO₃H and H₆P₂W₁₈O₆₂ · 18H₂O-Catalyzed, Three-Component, One-Pot Synthesis of Benzo[c]acridine Derivatives

Cited by 10 publications

References 17 publications

Catalytic Asymmetric Cyclizative Rearrangement of Anilines and Vicinal Diketones to Access 2,2‐Disubstituted Indolin‐3‐ones

Catalytic Asymmetric Cyclizative Rearrangement of Anilines and Vicinal Diketones to Access 2,2‐Disubstituted Indolin‐3‐ones

Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

ChemInform Abstract: NH₂SO₃H and H₆P₂W₁₈O₆₂·18H₂O‐Catalyzed, Three‐Component, One‐Pot Synthesis of Benzo[c]acridine Derivatives.

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NH2SO3H and H6P2W18O62 · 18H2O-Catalyzed, Three-Component, One-Pot Synthesis of Benzo[c]acridine Derivatives

Cited by 10 publications

References 17 publications

Catalytic Asymmetric Cyclizative Rearrangement of Anilines and Vicinal Diketones to Access 2,2‐Disubstituted Indolin‐3‐ones

Catalytic Asymmetric Cyclizative Rearrangement of Anilines and Vicinal Diketones to Access 2,2‐Disubstituted Indolin‐3‐ones

Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

ChemInform Abstract: NH2SO3H and H6P2W18O62·18H2 O‐Catalyzed, Three‐Component, One‐Pot Synthesis of Benzo[c]acridine Derivatives.

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NH₂SO₃H and H₆P₂W₁₈O₆₂ · 18H₂O-Catalyzed, Three-Component, One-Pot Synthesis of Benzo[c]acridine Derivatives

ChemInform Abstract: NH₂SO₃H and H₆P₂W₁₈O₆₂·18H₂O‐Catalyzed, Three‐Component, One‐Pot Synthesis of Benzo[c]acridine Derivatives.