Catalytic dehydrogenation of secondary amines with cobalt schiff base complex-oxygen system

Nishinaga, Akira; Yamazaki, Shigekazu; Matsuura, Teruo

doi:10.1016/s0040-4039(00)80431-1

Cited by 75 publications

(27 citation statements)

References 13 publications

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“…23 At the lower temperatures used here, however, use of 100 wt% activated carbon affords only 29% yield of product (Entry 15). Co(salen) has been used as a catalyst previously for dehydrogenation of the parent 1,2,3,4-tetrahydroquinoline at 60 °C, 24 but the presence of the 2-methyl group in tetrahydroquinaldine significantly attenuates the yield (28%, Entry 16).…”

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confidence: 99%

Catalytic Aerobic Dehydrogenation of Nitrogen Heterocycles Using Heterogeneous Cobalt Oxide Supported on Nitrogen-Doped Carbon

2015

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Dehydrogenation of (partially) saturated heterocycles provides an important route to heteroaromatic compounds. A heterogeneous cobalt oxide catalyst, previously employed for aerobic oxidation of alcohols and amines, is shown to be effective for aerobic dehydrogenation of various 1,2,3,4-tetrahydroquinolines to the corresponding quinolines. The reactions proceed in good yields under mild conditions. Other N-heterocycles are also successfully oxidized to their aromatic counterparts.

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confidence: 99%

Catalytic Aerobic Dehydrogenation of Nitrogen Heterocycles Using Heterogeneous Cobalt Oxide Supported on Nitrogen-Doped Carbon

2015

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“…[258] In some particular cases activated dimethyl sulfoxide oxidation (the Swern procedure) is used. [259,260] N-Alkyl and N-Aryl Aldimines Using Tetrapropylammonium Perruthenate; General Procedure: [246] A 10-mL reaction flask was charged sequentially with dry MeCN (2.5 mL), the amine (0.5 mmol), 4-powdered molecular sieves (250 mg), NMO (88 mg, 0.75 mmol), and TPAP (8.8 mg, 0.025 mmol).…”

Section: Nhbu Pr Nbumentioning

confidence: 99%

Product Class 7: Imines

Padwa¹,

Bellus²

2005

Category 4. Compounds With Two Carbon Heteroatom Bonds

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Compounds with the general structure R 1 R 2 C=NR 3 , referred to as imines, were first obtained by Schiff via condensation of ketones and aldehydes with primary amines. Therefore, the condensation products are also called Schiff bases. In addition, the nominations azomethine, ketimine (derived from ketones), aldimine (derived from aldehydes), and anil (derived from anilines) are in use. It is recommended that the terms imine(s), ketimine(s), or aldimine(s) are used, rather than Schiff base(s) or azomethine(s).Since imines have to be considered as analogues of carbonyl compounds, many of the chemical properties are similar to the latter. Imines are used in new C-C bond formations, and reactions with electrophiles (e.g., aldehydes, alkyl halides), and the C=N moiety can undergo nucleophilic reactions. Generally, imines are very useful compounds in organic synthesis, as they are used in several syntheses of aza-heterocyclic compounds. Most imines are stable in an alkaline medium and therefore can be dried over potassium hydroxide. In diluted acid, however, they are easily hydrolyzed. In many cases intermediary imines cannot be isolated because of their lability. The presence of a C=N bond creates the possibility for E/Z isomerism (syn/anti). It has been recognized that such geomet-

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“…Since N-benzylanilines can be oxidized into Nbenzylideneanilines under 1 atm oxygen in the presence of cobalt Schiff base complex 25 or Ru 2 (OAc) 4 Cl, 26 then 2-(benzylamino)benzamide may be turned into 2-phenylquinazolin-4(3H)-ones under air in the presence of a suitable catalyst. During the initial study, we found that copper(I) bromide directly transformed 2-(benzylamino)benzamide to 2-phenylquinazolin-4(3H)-ones under air at 120°C.…”

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Copper-Catalyzed Domino Synthesis of Quinazolin-4(3H)-ones from (Hetero)arylmethyl Halides, Bromoacetate, and Cinnamyl Bromide

Wei

Zhou

et al. 2013

Synthesis

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Alkyl halides, including heteroarylmethyl and arylmethyl halides, bromoacetate, and cinnamyl bromide, are readily prepared via halogenation from basic raw materials, even using green processes. It is essential to replace their downstream products with them to prepare medicinally important heterocycles quinazolin-4(3H)-ones. Copper(I) bromide catalyzed domino reaction of alkyl halides and anthranilamides under air affords 2-substituted quinazolin-4(3H)-ones in good to excellent yields and with wide functional group tolerance. A mechanism for a copper(I) bromide involved organometal-catalyzed reaction via a four-step domino reaction is proposed.

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Catalytic dehydrogenation of secondary amines with cobalt schiff base complex-oxygen system

Cited by 75 publications

References 13 publications

Catalytic Aerobic Dehydrogenation of Nitrogen Heterocycles Using Heterogeneous Cobalt Oxide Supported on Nitrogen-Doped Carbon

Catalytic Aerobic Dehydrogenation of Nitrogen Heterocycles Using Heterogeneous Cobalt Oxide Supported on Nitrogen-Doped Carbon

Product Class 7: Imines

Copper-Catalyzed Domino Synthesis of Quinazolin-4(3H)-ones from (Hetero)arylmethyl Halides, Bromoacetate, and Cinnamyl Bromide

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