The Rearrangement of Isoquinoline-<i>n</i>-oxides

Robison, Michael M.; Robison, Bonnie L.

doi:10.1021/jo01118a001

Cited by 50 publications

(10 citation statements)

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“…(C) Cross-coupling of benzylic alcohols with H 3 PO 2 The cross-coupling of benzylic alcohols with H 3 PO 2 catalyzed by palladium formed benzylic H-phosphinates, while the C-P bond formed efficiently without any prior activation. Coudray et al tested a broad range of benzylic alcohols and got the desired products in moderate to good yields.…”

Section: (B) Reduction Of Nitroarenes and Aryl Ketonesmentioning

confidence: 99%

Hypophosphorous Acid

Gao

2014

Synlett

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Kai Gao was born in 1987 and raised in Huanggang City, Hubei Province, China. He received his degree in chemistry from Hubei University of Science and Technology in 2012. Currently, he is carrying out research under the supervision of Prof. Bo Yang and Dr. Xiali Liao at the Kunming University of Science and Technology. His research focuses on the synthesis of novel phosphoramide ligands and small molecules with important bioactivities.

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Section: (B) Reduction Of Nitroarenes and Aryl Ketonesmentioning

confidence: 99%

Hypophosphorous Acid

Gao

2014

Synlett

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“…Traditionally, 2‐pyridones (i.e., 3 ) are prepared by treating N ‐oxides in refluxing acetic anhydride (Scheme A, 1 → 3 ), but an extra hydrolysis step is required. Although this method is useful, the yields are low because of the harsh reaction conditions and poor regioselectivity (C2 vs. C4) . In addition, the exposure of N ‐oxides to prolonged heating and high temperatures can cause safety concerns with regard to thermal stability and the risk of exothermic degradation.…”

Section: Introductionmentioning

confidence: 99%

A General and Efficient Synthesis of 2‐Pyridones, 2‐Quinolinones, and 1‐Isoquinolinones from Azine N‐Oxides

et al. 2016

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2‐Pyridones, 2‐quinolinones, and 1‐isoquinolinones are critical building blocks in medicinal chemistry. These N‐heterocycles, however, remain a challenge to synthesize by current methods. A mild, general, and efficient approach for the synthesis of these hydroxyl N‐heteroarenes was developed by employing bromotripyrrolidinophosphonium hexafluorophosphate (PyBroP) as an activating agent and sodium acetate/water as the base/nucleophile combination. The reaction mechanism, especially the dual function of sodium acetate as the base and nucleophile, has been proposed on the basis of results from isotopic labeling experiments.

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“…The following compounds were prepared by previously de- (13), and 4-hydroxy-3-carbomethoxy-l-2H-isoquinolone (1 1) (16).…”

Section: Methodsmentioning

confidence: 83%