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Usage

InChI:InChI=1/C11H9NO2/c13-10-8-5-1-3-7-4-2-6-12(9(7)8)11(10)14/h1,3,5H,2,4,6H2

Upstream product

• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 79-37-8 oxalyl dichloride 
• 924-44-7 glyoxylic acid ethyl ester 
• 5840-01-7 5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline 
• 201230-82-2 carbon monoxide 

Relevant academic research and scientific papers

Spiro[4H-pyran-3,3′-oxindoles] Derived from 1,2,3,4-Tetrahydroquinoline

Three-component reactions of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione with malononitrile, or ethyl cyanoacetate, and cyclic six-membered or a five-membered 1,3-diketone, produce spiro[4H-pyran-3,3′-oxindoles].

Spiro[3H-pyrazole-3,3′-oxindoles] Derived from 1,2,3,4-Tetrahydroquinoline

Aldol condensation of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione with aryl methyl ketones generates 3-(aroylmethylidene)oxindoles, which react with hydrazine to generate tricyclic spiro[3H-pyrazole-3,3′-oxindoles].

Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides

Dearomatisation of indole derivatives to the corresponding isatin derivatives has been achieved with the aid of visible light and oxygen. It should be noted that isatin derivatives are highly important for the synthesis of pharmaceuticals and bioactive compounds. Notably, this chemistry works excellently with N-protected and protection-free indoles. Additionally, this methodology can also be applied to dearomatise pyrrole derivatives to generate cyclic imides in a single step. Later this methodology was applied for the synthesis of four pharmaceuticals and a pesticide called dianthalexin B. Detailed mechanistic studies revealed the actual role of oxygen and photocatalyst.

Three-component synthesis of novel spiro[4H-pyran-3,3-oxindoles] using 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione

One-pot, three-component reactions of the tricyclic isatin 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione with variously substituted aryl cyanomethyl ketones and malononitrile, or ethyl cyanoacetate, generates spiro[4H-pyran-3,3-oxindoles], such as, 2-amino-2'-oxo-6-(phenyl)-5',6'-dihydro-2'H,4'H-spiro[pyran-4,1'-pyrrolo[3,2,1-ij]quinoline]-3,5-dicarbonitrile.

Hexahydrospiro-pyrazolo[3,4-b]pyridine-4,1′-pyrrolo[3,2,1-ij]quinolines Derived from 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione

The tricyclic isatin, 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione (1), reacts with a combination of an aryl cyanomethyl ketone 8 and a 5-amino-1-arylpyrazole 7 to generate spirocyclic products 9.

Active sp3 C-H Bond Oxidation Initiated sp3-sp2 Consecutive C-H Functionalization of N-Arylglycine Amides: Construction of Isatins

In the presence of catalytic triarylamine radical cation, an sp3-sp2 consecutive C-H functionalization of N-arylglycine amides was achieved, providing a series of isatin derivatives in high yields. In this transformation, the initial aerobic oxidation of the relatively active sp3 C-H bonds triggered the following intramolecular cyclization, in which the aniline group was employed as a removable auxiliary group to enable the consecutive process.

From anilines to isatins: Oxidative palladium-catalyzed double carbonylation of C-H bonds

A novel palladium-catalyzed C-H double carbonylation introduces two adjacent carbonyl groups for the synthesis of isatins from readily available anilines. The reaction proceeds under atmospheric pressure of CO with high regioselectivity and without any additives. Density functional theory investigations indicate that the palladium-catalyzed double carbonylation catalytic cycle is plausible.

Copper-catalyzed selective oxidative acylation of secondary anilines with ethyl glyoxalate: Domino synthesis of indoline-2,3-diones

A novel, easy and useful copper-catalyzed selective acylation of secondary anilines with ethyl glyoxalate has been developed, and the corresponding indoline-2,3-dione derivatives were prepared. The procedure comprises the sequential intermolecular copper-catalyzed selective oxidative ortho-site aromatic acylation of the NH group in secondary anilines and intramolecular nucleophilic attack of the NH group to the ester. The inexpensive, easy and efficient method should provide a new strategy for synthesis of dicarbonyl compounds. Copyright

Synthesis and anti-leukaemic activity of pyrrolo[3,2,1-hi]indole-1,2- diones, pyrrolo[3,2,1-ij]quinoline-1,2-diones and other polycyclic isatin derivatives

To further expand the structure-cytotoxic activity relationships of isatin derivatives and to reduce flexibility in substituent groups at nitrogen, 20 analogues incorporating a ring system between the N1 and C7 atoms of isatin were prepared using a variety of synthetic strategies. This yielded pyrroloindole-, pyrroloquinoline-, pyrroloacridine-, pyrrolophenanthridine- and benzopyrrolophenanthridine-based systems with embedded isatin moieties, the latter possessing a novel carbon skeleton. These compounds were subsequently assessed for their in vitro cytotoxicity against human U937 lymphoma cells, with the brominated pyrroloacridine dione 27 showing the most promising activity (IC50 3.01 μM) after 24 h.

Therapeutic agents of metabolic bone disease

New use of cyclic anthranilic acid derivatives of the following formula, STR1 wherein R1, R2 and R3 each independently indicate a hydrogen atom, chlorine atom, lower alkyl group having 1 to 3 carbon atoms, lower alkoxy group having 1 to 3 carbon atoms, amino group, nitro group, hydroxy group, sulfonamide group, trifluoromethyl group, cyano group, carboxyl group, carbamoyl group, acetyl group, benzoymethyl group which may be substituted, methylthio group, phenylethnyl group which may be substituted, alkanoylamino group having 1 to 3 carbon atoms, benzoylamino group which may be substituted, alkylsulfonylamino group having 1 to 3 carbon atoms or phenylsulfonylamino group which may be substituted; R4 and R5 each independently indicate a hydrogen atom, lower alkyl group having 1 to 3 carbon atoms, cyano group, carboxyl group, hydroxymethyl group, phenyl group which may be substituted or benzoyl group, R6 indicates a hydrogen atom, lower alkyl group having 1 to 3 carbon atoms or benzyl group; X indicates a methylene group, oxygen atom, sulfur atom, sulfinyl group or sulfonyl group, their acid or alkali salts thereof as therapeutic agents for metabolic bone diseases is described.