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83-26-1

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Palladium-Catalyzed Carbonylative Annulation Reactions Using Aryl Formate as a CO Source: Synthesis of 2-Substituted Indene-1,3(2H)-dione Derivatives
An efficient synthesis of 2-substituted indene-1,3(2H)-diones from stable and readily available 1-(2-halophenyl)-1,3-diones by employing phenyl formate as a CO source has been developed. The reaction occurred via palladium-catalyzed intramolecular carbonylative annulation using K3PO4 as a base and DMSO as a solvent at 95 °C. In this protocol, the reaction showed a broad substrate scope with good to excellent yields.
Zhang, Ying,Chen, Jing-Lei,Chen, Zhen-Bang,Zhu, Yong-Ming,Ji, Shun-Jun
p. 10643 - 10650
(2015/11/18)

Synthesis and Chemical Reactivity of Indenoisoxazoles
Treatment of 2-pivaloyl-1,3-indandione (1) with hydroxylamine under acidic conditions, results in formation of 8-t-butylindenoisoxazol-7-one (2) while treatment of the triketone with hydroxylamine at neutral or basic pH gave 6 which upon cyclization gave the isomeric 3-t-butylindenoisoxazol-4-one (7).Compound 7 was readily reduced to amine 12 by treatment with hydrazine or hydrogen over platinum.The amine, although quite unreactive, was converted to 3-t-butylindenopyrazol-4-one (13) with hydrazine or reduced to 15 and 16 with sodium, in liquid ammonia and alcohol.Surprisingly, the amine 3 obtained from isoxazole 2 gave reduction product 15 from a sodium-liquid ammonia reduction and not the expected product 18.Spectral evidence for each of the structures is discussed.
Lemke, Thomas L.,Sawhney, Kailash N.,Lemke, B. Kaye
p. 363 - 368
(2007/10/02)

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Chemical Properties

Appearance/Colour :solid
Melting Point: 155 - 156 C
Boiling Point: 82.987°C at 760 mmHg
Flash Point:-13.169°C
Density: 1.1914 (rough estimate)
Solubility:Soluble in most organic solvents (Worthing and Hance, 1991)
Storage Temp.:APPROX 20°C
Vapor Pressure: 76.833mmHg at 25°C
Refractive Index: 1.5557 (estimate)
PKA: 3.47±0.10(Predicted)
Merck: 13,7526
BRN: 2051258
PSA: 51.21000
LogP: 2.29700

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