Sulfamic acid as energy efficient catalyst for synthesis of flurophores, 1-H-spiro [isoindoline-1,2′-quinazoline]-3,4′(3′H)-diones

Mane, Mansing M.; Pore, Dattaprasad M.

doi:10.1007/s12039-016-1047-7

Cited by 18 publications

(5 citation statements)

References 39 publications

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“…o -Aminobenzamides 1a , 1b undergo TsOH-catalyzed condensation with acenaphthenequinone ( 2 ) to yield spiro(dihydroquinazolinone)s 4a , 4b in 88–94% yield (Scheme ). Similar Brønsted acid , or Lewis acid-catalyzed syntheses of spiro(dihydroquinazolinone)s have been reported. Dihydroquinazolinone 5a was prepared in a similar manner from butanedione ( 3 , Scheme ).…”

Section: Resultssupporting

confidence: 64%

Autoxidation of Heterocyclic Aminals

Zhai

Jordan

2017

ACS Omega

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The autoxidation reactions of 2-acyl-2,3-dihydroquinazolin-4(1 H )-ones 4a and 5a and 2,2′-bis(dihydroquinazolinone) 6a are described. These reactions generate aminyl radicals that undergo β-C–C cleavage, and subsequent reactions of the resulting C-based radicals with O 2 lead to diverse products with good selectivity, depending on the structure of the substrate. Oxidation of 4a , in which the 2-acyl group is part of a cyclic acenaphthenone unit, yields a heterocyclic C -hydroperoxylaminal via 1,2-acyl migration. Oxidation of 5a , which contains a 2-acetyl group, yields peracetic acid and a quinazolinone product. Oxidation of 6a forms a bis(quinazolinone) by net dehydrogenation.

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Section: Resultssupporting

confidence: 64%

Autoxidation of Heterocyclic Aminals

Zhai

Jordan

2017

ACS Omega

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“…The spiro derivatives of quinazoline are commonly prepared either via a 3-component reaction of isatoic anhydride, amine and cyclic ketone [19][20][21][22][23] or the reaction of 2-aminobenzamide with cyclic ketone. [24][25][26][27][28][29][30][31][32][33] In general, isatin has been used as the cyclic ketone or one of the ketones among various ketone derivatives employed in these reactions to afford the spiroindoline-3,2'-quinazoline derivatives. A range of conditions including various catalysts, solvents (including aqueous and non-aqueous media), solvent-free condition, ultrasound or microwave irradiation etc have been explored for this purpose.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Docking and In Vitro Evaluation of Spiroindoline‐3,2’‐Quinazoline Derivatives

Addu,

Miriyala,

Kapavarapu

et al. 2023

ChemistrySelect

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The Wang‐OSO3H catalyzed synthesis of a series of spiroindoline‐3,2’‐quinazoline derivatives and their in silico and in vitro evaluation against MtbCM (Mycobacterium tuberculosis Chorismate Mutase) are disclosed. Initially, a library of small molecules based on spiroindoline‐3,2’‐quinazoline framework was constructed. The reaction of 2‐aminobenzamide with appropriate isatin derivatives in the presence of Wang‐OSO3H under ultrasound irradiation was used for this purpose. The reaction proceeded under mild conditions to afford the desired products in good yields within a short duration. With the use of heterogeneous catalyst, inexpensive solvent as reaction media, and ultrasound as the source of green energy the methodology appeared to be a useful alternative to the previously reported methods. The in silico docking of all the synthesized compounds into the MtbCM (PDB: 2FP2) revealed that the binding of these compounds took place on the external surface pockets of the MtbCM active site cavity mainly in two different clusters. Three compounds that interacted well with MtbCM also showed good (57–64 %) inhibition of MtbCM in vitro when tested at 10 μM. Based on in silico and in vitro studies along with the ADME predictions these three spiroindoline‐3,2’‐quinazoline derivatives were identified as pre‐hits.

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“…74 The products were found to be fluorescent with absorption in UV region (302, 362 nm) and emission in visible region (413-436 nm) with Stokes shift of 44-72 nm.…”

Section: Scheme 33mentioning

confidence: 98%