494. The preparation of α-N-alkylamino-nitriles, -amides, and -acids

Cook, A. H.; Cox, S. F.

doi:10.1039/jr9490002334

Cited by 16 publications

(5 citation statements)

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“…With bulkier aldehydes, the cis -1,4-/ trans -1,4-ratio became larger, indicative of a Curtin−Hammett situation where equilibrium existed among allylindium species. The opposite selectivities obtained from cyclopentenyl acetate 8 (hydroxamic acid-containing) and 9 (no hydroxamic acid) further supported the suggested directing effect of hydroxamate group …”

Section: Resultsmentioning

confidence: 66%

Stereo- and Regioselectivity of Pd⁰/InI-Mediated Allylic Additions to Aldehydes and Ketones. In Situ Generation of Allylindium(III) Intermediates from N-Acylnitroso Diels−Alder Cycloadducts and 1-Amino-4-acetoxycyclopentenes

et al. 2002

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Acylnitroso Diels-Alder cycloadduct (11, 37, and 45)- and cyclopentenyl acetate (8 and 9)-derived allylindium(III) species were generated in situ from palladium(0) catalysts and indium(I) iodide, and the stereo- and regiochemistry of their additions to aldehydes and ketones were investigated. Solvent, catalyst, and ionic effects were examined for the reaction of N-acetyl cycloadduct (11) and benzyloxyacetaldehyde (10). The solvent mixture of THF/H(2)O with Pd(OAc)(2).PPh(3) catalysis was found to be optimal. The addition of N-acetyl cycloadduct to aliphatic aldehydes afforded products in good yields and high regio- and stereoselectivity, with the cis-1,4-isomers constituting 90-95% of the products. The reactions with N-Boc (37a) and N-methylcarbamate (37b) cycloadducts also gave the cis-1,4-products predominantly. The same regio- and stereoselectivity applied to the reactions of 4-acetoxy-1-(N-hydroxyphenyacetamido)cyclopentene (8). 4-Acetoxy-1-phenylacetamidocyclopentene (9), however, afforded trans-1,4-products exclusively. Mechanistic speculations involving chelated transition states are described.

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Section: Resultsmentioning

confidence: 66%

Stereo- and Regioselectivity of Pd⁰/InI-Mediated Allylic Additions to Aldehydes and Ketones. In Situ Generation of Allylindium(III) Intermediates from N-Acylnitroso Diels−Alder Cycloadducts and 1-Amino-4-acetoxycyclopentenes

et al. 2002

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“…Furthermore, the acidic reductive system does not cleave the ether group present in the various 9,10-anthraquinones. 6 Under the same condition, ethyl 1¢anthracenoxyacetate (3i) could be selectively obtained from the reduction of the related 9,10-anthraquinone derivative 1i without affecting the ester group in 1i.…”

Section: Methodsmentioning

confidence: 99%

“…3 The reduction reaction can usually be achieved by either excess sodium borohydride 4 or complicated sodium borohydride-metal (Na or Li)-ammonia/pchloranil system 5 in a stepwise procedure. Although onestep reductive system of zinc/aqueous ammonia, 6 zinc/ aqueous sodium hydroxide 7 or zinc/cyclohexyl-p-toluenesulfonate/hot trichlorobenzene 8 are sometimes possible, they are often unreliable or of limited substrate and preparative value. Herein we report a new convenient method to alkoxyanthracenes.…”

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confidence: 99%

A New Convenient Synthesis of Alkoxyanthracenes from Alkoxy-9,10-anthraquinones

Lu¹,

Chen²,

Zhu³

et al. 2003

Synthesis

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Methoxy-9,10-anthraquinones with mono-, di-and tetraether groups at different positions 1a-h can be directly reduced to the corresponding methoxyanthracenes 3a-h in moderate to good yields by zinc in refluxing acetic acid. Under similar conditions, ethyl 1¢-anthracenoxyacetate (3i) with the ester group unaffected and 1,8-oxybis(ethyleneoxyethyleneoxy)anthracene (5) were also conveniently synthesized in 65 and 70% yields, respectively.

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“…NPAN raw material was synthesized starting from Nmethylanilide (I) [7][8][9][10][11]. The synthesis procedure is shown in scheme (Fig.…”

Section: Synthesismentioning

confidence: 99%

Synthesis, crystal growth and characterization of organic NLO material: N-(4-nitrophenyl)-N-methyl-2-aminoacetonitrile (NPAN)

Gao

Chen

Wang

et al. 2006

Journal of Crystal Growth

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494. The preparation of α-N-alkylamino-nitriles, -amides, and -acids

Cited by 16 publications

References 0 publications

Stereo- and Regioselectivity of Pd⁰/InI-Mediated Allylic Additions to Aldehydes and Ketones. In Situ Generation of Allylindium(III) Intermediates from N-Acylnitroso Diels−Alder Cycloadducts and 1-Amino-4-acetoxycyclopentenes

Stereo- and Regioselectivity of Pd⁰/InI-Mediated Allylic Additions to Aldehydes and Ketones. In Situ Generation of Allylindium(III) Intermediates from N-Acylnitroso Diels−Alder Cycloadducts and 1-Amino-4-acetoxycyclopentenes

A New Convenient Synthesis of Alkoxyanthracenes from Alkoxy-9,10-anthraquinones

Synthesis, crystal growth and characterization of organic NLO material: N-(4-nitrophenyl)-N-methyl-2-aminoacetonitrile (NPAN)

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494. The preparation of α-N-alkylamino-nitriles, -amides, and -acids

Cited by 16 publications

References 0 publications

Stereo- and Regioselectivity of Pd0/InI-Mediated Allylic Additions to Aldehydes and Ketones. In Situ Generation of Allylindium(III) Intermediates from N-Acylnitroso Diels−Alder Cycloadducts and 1-Amino-4-acetoxycyclopentenes

Stereo- and Regioselectivity of Pd0/InI-Mediated Allylic Additions to Aldehydes and Ketones. In Situ Generation of Allylindium(III) Intermediates from N-Acylnitroso Diels−Alder Cycloadducts and 1-Amino-4-acetoxycyclopentenes

A New Convenient Synthesis of Alkoxyanthracenes from Alkoxy-9,10-anthraquinones

Synthesis, crystal growth and characterization of organic NLO material: N-(4-nitrophenyl)-N-methyl-2-aminoacetonitrile (NPAN)

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Stereo- and Regioselectivity of Pd⁰/InI-Mediated Allylic Additions to Aldehydes and Ketones. In Situ Generation of Allylindium(III) Intermediates from N-Acylnitroso Diels−Alder Cycloadducts and 1-Amino-4-acetoxycyclopentenes

Stereo- and Regioselectivity of Pd⁰/InI-Mediated Allylic Additions to Aldehydes and Ketones. In Situ Generation of Allylindium(III) Intermediates from N-Acylnitroso Diels−Alder Cycloadducts and 1-Amino-4-acetoxycyclopentenes