Copper‐Catalyzed Domino C−C Bond Cleavage of 2,3‐Unsubstituted Indoles/Indolines and Oxindoles <i>via</i> Oxidation and Directed Insertion of 2‐Aminopyridines: Direct Access to Quinazolinediones

Ravi, Owk; Ramaraju, Andhavaram; Sridhar, Balasubramanian; Bathula, Surendar Reddy

doi:10.1002/adsc.201800536

Cited by 7 publications

(6 citation statements)

References 56 publications

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“…3-(4-Methylpyridin-2-yl)quinazoline-2,4(1H,3H)-dione 3a [58]. White powder; 70% yield (35 mg); mp 266-268 • C. 1 H NMR (400 MHz, DMSO-d 6 ) δ 11.63 (s, 1H), 8.51-8.41 (m, 1H), 7.99-7.89 (m, 1H), 7.78-7.67 (m, 1H), 7.39-7.31 (m, 2H), 7.31-7.20 (m, 2H), 2.39 (s, 3H).…”

Section: Synthesis Of Quinazoline-24-dionesmentioning

confidence: 99%

Synthesis of 3-(Pyridin-2-yl)quinazolin-2,4(1H,3H)-diones via Annulation of Anthranilic Esters with N-pyridyl Ureas

Baykova

Geyl

Baykov

et al. 2023

IJMS

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A new route for the synthesis of quinazolin-2,4(1H,3H)-diones and thieno [2,3-d]pyrimidine-2,4(1H,3H)-diones substituted by pyridyl/quinolinyl moiety in position 3 has been developed. The proposed method concluded in an annulation of substituted anthranilic esters or 2-aminothiophene-3-carboxylates with 1,1-dimethyl-3-(pyridin-2-yl) ureas. The process consists of the formation of N-aryl-N′-pyridyl ureas followed by their cyclocondensation into the corresponding fused heterocycles. The reaction does not require the use of metal catalysts and proceeds with moderate to good yields (up to 89%). The scope of the method is more than 30 examples, including compounds with both electron-withdrawing and electron-donating groups, as well as diverse functionalities. At the same time, strong electron-acceptor substituents in the pyridine ring of the starting ureas reduce the product yield or even prevent the cyclocondensation step. The reaction can be easily scaled to gram quantities.

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Section: Synthesis Of Quinazoline-24-dionesmentioning

confidence: 99%

Synthesis of 3-(Pyridin-2-yl)quinazolin-2,4(1H,3H)-diones via Annulation of Anthranilic Esters with N-pyridyl Ureas

Baykova

Geyl

Baykov

et al. 2023

IJMS

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“…64 The title compound was synthesized according to the general procedure and obtained as a white solid (35 mg, 73%); 3:7 (EA/Hexane) as the eluent; 1 3-(5-Methylpyridin-2-yl)quinazoline-2,4(1H,3H)-dione (2p). 65 The title compound was synthesized according to the general procedure and obtained as a white solid (31 mg, 62%); 3:7 (EA/ Hexane) as the eluent; 6-Fluoro-3-phenylquinazoline-2,4(1H,3H)-dione (2r). 60 The title compound was synthesized according to the general procedure and obtained as a white solid (39 mg, 76%); 3:7 (EA/Hexane) as the eluent; 1 6-Chloro-3-phenylquinazoline-2,4(1H,3H)-dione (2s).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Metal-Free N–H/C–H Carbonylation by Phenyl Isocyanate: Divergent Synthesis of Six-Membered N-Heterocycles

et al. 2022

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We disclose a method using phenyl isocyanate to synthesize carbonyl-containing N-heterocycles. The metal-free novel approach for both N–H and C–H carbonylation processes was successfully refined, delivering a range of synthetically valuable derivatives of quinazoline-2,4(1H,3H)-dione, 2H-benzo[e] [1,2,4] thiadiazin-3(4H)-one 1,1-dioxide, and pyrrolo[1,2-a] quinoxalin-4(5H)-one. The protocol features broad substrates with diverse reactions suitable for excellent yields, mild conditions, and good functional group compatibility. Moreover, the applicability of the reaction was characterized by gram-scale synthesis and synthetic transformations for drug molecules.

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“…Also, a nickel catalyzed synthesis of quinazolinediones from isatoic anhydrides and isocyanides was reported by Beutner in 2017 (Equation 4) . Very recently, Bathula and his co‐workers, reported a copper‐catalyzed domino C–C bond cleavage of 2,3‐unsubstituted indoles/indolines and oxindoles via oxidation and directed insertion of 2‐aminopyridines to access quinazolinediones (Equation 5) …”

Section: Introductionmentioning

confidence: 98%

Copper‐Mediated Direct Cyanatation of Benzamides: A New Approach to the Synthesis of Quinazolinediones

et al. 2020

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Copper mediated cyanatation of N‐(quinoline‐8‐yl)benzamides with cyanate salts and subsequent intramolecular cyclization of the resulting product was accomplished. Different derivatives of quinazoline‐2,4(1H,3H)‐dione bearing quinoline‐8‐yl directing group were readily prepared in moderate to high yields by this methodology from easily accessible starting materials through cascade directed C–H bond functionalization/annulation reactions.

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Copper‐Catalyzed Domino C−C Bond Cleavage of 2,3‐Unsubstituted Indoles/Indolines and Oxindoles via Oxidation and Directed Insertion of 2‐Aminopyridines: Direct Access to Quinazolinediones

Cited by 7 publications

References 56 publications

Synthesis of 3-(Pyridin-2-yl)quinazolin-2,4(1H,3H)-diones via Annulation of Anthranilic Esters with N-pyridyl Ureas

Synthesis of 3-(Pyridin-2-yl)quinazolin-2,4(1H,3H)-diones via Annulation of Anthranilic Esters with N-pyridyl Ureas

Metal-Free N–H/C–H Carbonylation by Phenyl Isocyanate: Divergent Synthesis of Six-Membered N-Heterocycles

Copper‐Mediated Direct Cyanatation of Benzamides: A New Approach to the Synthesis of Quinazolinediones

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