The Stereochemistry of Organometallic Compounds. XLII. The Preparation of [2,1-b]Quinazolines Involving Rhodium-Catalysed Hydroformylation of 2-Amino-N-Alkenylbenzylamines

Campi, Eva M.; Habsuda, Jana; Jackson, W. R.; Jonasson, Catrin; McCubbin, Quentin J.

doi:10.1071/ch9952023

Cited by 29 publications

(27 citation statements)

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“…13 C{ 1 H} NMR (151 MHz, chloroform- d ) δ 141.9, 127.6, 126.9, 119.3, 118.3, 114.7, 70.4, 56.1, 52.1, 31.8, 25.3, 21.6. NMR spectra are in accordance with literature data …”

Section: Experimental Sectionsupporting

confidence: 83%

“…The obtained dark yellow oil was purified by column chromatography (eluent: hexane/ethyl acetate/triethylamine = 1:2:0.1 R f 0.3) to afford 1.52 g (62%) of the product as a slightly yellow solid. Mp: 71–73 °C (lit . mp 71–72 °C).…”

Section: Experimental Sectionmentioning

confidence: 99%

“…DMF was distilled over CaH 2 . 1 H and 13 C NMR spectra were recorded on Bruker AV-300, AV-400, AV-600, and Varian Inova-400 spectrometers at ambient temperature. Chemical shifts δ are reported in ppm using the solvent resonance signal as an internal standard.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…Chemical shifts are reported in parts per million relative to CHCl 3 (7.26 and 77.16 ppm for 1 H and 13 C, respectively), DMSO (2.50 ppm for 1 H, 39.52 for 13 C). All 13 C NMR spectra were recorded with proton decoupling.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family

et al. 2020

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A total synthesis of the vasicinone family of natural products from bulk chemicals was developed. Reductive condensation of o-nitrobenzaldehydes with amines utilizing iron pentacarbonyl as a reducing agent followed by subsequent oxidation leads to a great variety of polycyclic nitrogen-containing heterocycles under mild conditions. Enantiomerically pure vasicinone, rutaecarpine, isaindigotone, and luotonin were synthesized from readily available starting materials like hydroxyproline, nitrobenzaldehyde, pyrrolidine, and piperidine in two to four operational steps without chromatography. The antifungal activity of all products was tested.

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“…13 C{ 1 H} NMR (151 MHz, chloroform- d ) δ 141.9, 127.6, 126.9, 119.3, 118.3, 114.7, 70.4, 56.1, 52.1, 31.8, 25.3, 21.6. NMR spectra are in accordance with literature data …”

Section: Experimental Sectionsupporting

confidence: 83%

Section: Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family

et al. 2020

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“…Reductive carbonylation of N-allyl-2-aminobenzylamine 103 with carbon monoxide and hydrogen over a rhodium catalyst yielded dihydrodeoxyvasicine 104 in 96% yield. 65 The methylallyl analogue 105 yielded mixtures of the hexahydropyrroloquinazoline 106 and the tetrahydro derivative 107, while the homologues 108 and 109 afforded even more complex mixtures of fused quinazoline products.…”

Section: Structural and Synthetic Studiesmentioning

confidence: 99%

Quinoline, quinazoline and acridone alkaloids

Michael¹

1997

Nat. Prod. Rep.

346

113

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The Hydroformylation Reaction

et al. 2000

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The reaction of 1‐alkenes with carbon monoxide and hydrogen in the presence of a catalyst gives the corresponding homologous aldehydes. The discovery of this reaction was made by Roelen in 1938 using Co 2 (CO) 8 as the catalyst at high temperature (120–170°) and high pressure of carbon monoxide/hydrogen (200–300 bar). This reaction has been called the “Oxo reaction”, “Roelen reaction” or “hydroformylation”. Hydroformylation is a general term indicating that both a hydrogen and a formyl group are introduced to unsaturated bonds, especially olefins. Later this reaction was developed as an industrial process, i.e., the Oxo Process, for the production of alkanals from 1‐alkenes using a cobalt or rhodium catalyst. Most noteworthy is the conversion of propene to butanal, which can be subsequently hydrogenated to 1‐butanol or converted to 2‐ethylhexanol by self‐aldol condensation. 2‐Ethylhexanol, a crucial intermediate for the production of ester‐type plasticizers, is the most important bulk chemical produced by the Oxo Process. A variety of transition metal catalysts other than Co 2 (CO) 8 have been investigated, including phosphine complexes of cobalt and hydridocobalt clusters. Platinum and ruthenium complexes show reasonably good catalytic activities, but modified cobalt catalysts are still much more advantageous. However, various rhodium complexes demonstrate higher catalytic activity (10 3 –10 4 times) than the cobalt complexes. Although the price of rhodium is higher than cobalt, reactions using rhodium catalysts require lower temperature (50–80°) and pressure (10–50 atm). Other important commercial applications of hydroformylation include the production of long‐chain alcohols from C 5 –C 17 isomeric linear alkenes. These long‐chain alcohols serve as intermediates for lubricants, plasticizers and detergents. The hydroformylation of ethene to propanal is another important Oxo Process. In this chapter, the authors put clear emphasis on the scope of the hydroformylation reaction in organic synthesis. In this context, there is a relevant review in 1987 of the hydroformylation of functionalized alkenes. The hydroformylation reaction now can be performed under very mild conditions using a variety of functionalized alkenes. Reactions in aqueous biphase, supercritical carbon dioxide or fluorous biphase have recently emerged in response to separation and environmental issues. In fact, a highly efficient Oxo Process using a water‐soluble rhodium catalyst in aqueous biphasic conditions has been commercialized by Ruhrchemie/Rhône‐Poulenc for the production of butanal. Asymmetric hydroformylation of prochiral olefins catalyzed by enantiopure rhodium complexes has been developed to the level that practical applications appear possible. Although the reactions of formaldehyde, oxiranes, and others with carbon monoxide and hydrogen in the presence of transition metal catalyst could be considered as variations of hydroformylation, this chapter only deals with hydroformylation of carbon‐carbon multiple bonds.

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The Stereochemistry of Organometallic Compounds. XLII. The Preparation of [2,1-b]Quinazolines Involving Rhodium-Catalysed Hydroformylation of 2-Amino-N-Alkenylbenzylamines

Cited by 29 publications

References 0 publications

Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family

Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family

Quinoline, quinazoline and acridone alkaloids

The Hydroformylation Reaction

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