One-pot synthesis of 4-aminobicyclo[2.2.2]octan-2-ones

Weis, Robert; Schweiger, Klaus; Seebacher, Werner; Belaj, Ferdinand

doi:10.1016/s0040-4020(98)00864-3

Cited by 37 publications

(5 citation statements)

References 37 publications

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“…The solvent was evaporated in vacuo giving a residue which was further purified by use of CC (eluent: 8:8:1 benzene/ chloroform/ethanol) affording 5b (15.4 g, 13.5%) as a yellowish resin. Spectral data corresponded well with those reported [ 2 ].…”

Section: Methodssupporting

confidence: 89%

“…We have previously reported [ 2 ] the formation of 4-aminobicyclo[2.2.2]octan-2-ones from ammonium thiocyanates and benzylidene acetone in a one-pot reaction, proposing the following mechanism for this transformation: benzylidene acetone ( 1 ) reacts with dialkylammonium thiocyanates 2a-d in an initial step to give the enammonium salts 3a-d , followed by a Diels-Alder reaction of the latter with unreacted 1 . The thus formed 4-acetylcyclohex-1-enylammonium salts 4a-d then cyclize to give the bicyclic compounds 5a-d ( Scheme 1 ).…”

Section: Resultsmentioning

confidence: 99%

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Investigations on the Formation of 4-Aminobicyclo[2.2.2]-octanones

et al. 2005

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Benzylidene acetone reacts with thiocyanates derived from secondary amines in a one-pot reaction to give 4-aminobicyclo[2.2.2]octan-2-ones. The reaction mixture was investigated for the presence of possible intermediates using GC-MS. These intermediates – diketones and enamines – were prepared and exposed to the same reaction conditions to examine the reaction mechanism. The reaction of ethyl styryl ketone with thiocyanates of secondary amines yielded cyclohexanone derivatives instead of the expected bicyclo-octanones. Their structures were established by means of a single crystal structure analysis.

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Section: Methodssupporting

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Investigations on the Formation of 4-Aminobicyclo[2.2.2]-octanones

et al. 2005

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“…Compounds 1a-d, 2a, b, and 3a, c, d were prepared following reported procedures (Seebacher et al, 2005;Weis et al, 1998;Weis et al, 2003).…”

Section: Synthesesmentioning

confidence: 99%

“…Compounds 1 were prepared from benzylidene acetone and dialkylammonium thiocyanates in one-pot reactions in boiling toluene or dimethylformamide using a water separator (Weis et al, 1998, Weis et al, 2003. Tosylhydrazones 2 were synthesized from ketones 1 and tosylhydrazine in refluxing methanol (Seebacher et al, 2005).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis of bicyclic amines and their activities against Trypanosoma brucei rhodesiense and Plasmodium falciparum K 1

et al. 2008

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New alkenes, aziridines, and diamines were prepared from antiprotozoal 4-dialkylaminobicyclo[2.2.2]octan-2-imines to investigate the influence of several functional groups in position 2 of the ring skeleton on the antitrypanosomal and antiplasmodial activities. They were synthesized from 4-dialkylaminobicyclo[2.2.2]octan-2-imines and tested for their activities against Trypanosoma b. rhodesiense and Plasmodium falciparum K1 (resistant to chloroquine and pyrimethamine) using in vitro microplate assays. 4-Aminobicyclo[2.2.2]oct-2-enes and 3-azatricyclo[3.2.2.0(2,4)]nonylamines exhibit similar antiprotozoal activities as 4-aminobicyclo[2.2.2] octanes. 4-Aminobicyclo[2.2.2]oct-2-ylamines and their N-benzyl derivatives showed decreased antiplasmodial but enhanced antitrypanosomal (IC50 = 0.22-0.41 microM) activities compared to their parent oximes and to formerly synthesized 4-amino-2-azabicyclo[3.2.2]nonanes. Some of the 4-aminobicyclo[2.2.2]oct-2-ylamines exhibit moderate in vivo activity in mice against Trypanosoma brucei brucei.

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“…Weis reported the one-pot synthesis of bicyclo[2.2.2]octan-2-ones from dialkylammonium rhodanides and benzylidene acetone. And the author thinks that the mechanism of the reaction includes a Diels–Alder step (Figure b) . As a continuation of our interest in developing a methodology of rapid access to diverse scaffolds for natural products, herein we present a successive Michael addition and subsequent decarboxylative–Mannich process, representing a combination strategy for a one-pot organocatalytic reaction from α,β-unsaturated ketones and amino acids (Figure c).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Functionalized Bicyclo[2.2.2]octan-2-ones Skeleton via Tandem Process of Amino Acid Involved Formal [4 + 2] and Decarboxylative–Mannich Sequence

Mao

Nie

et al. 2021

J. Org. Chem.

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An efficient approach to a functionalized bicyclo[2.2.2]octan-2-one scaffold has been developed through a one-pot cascade process including amino acid involved successive Michael addition and decarboxylative−Mannich sequence. Starting from α,β-unsaturated ketones and amino acids, a series of desired products 7a−7m and 8a−8o were obtained with moderate yields. In addition, the tandem process was reasonably explained by the results of DFT calculations. Article pubs.acs.org/joc

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One-pot synthesis of 4-aminobicyclo[2.2.2]octan-2-ones

Cited by 37 publications

References 37 publications

Investigations on the Formation of 4-Aminobicyclo[2.2.2]-octanones

Investigations on the Formation of 4-Aminobicyclo[2.2.2]-octanones

Synthesis of bicyclic amines and their activities against Trypanosoma brucei rhodesiense and Plasmodium falciparum K 1

Synthesis of Functionalized Bicyclo[2.2.2]octan-2-ones Skeleton via Tandem Process of Amino Acid Involved Formal [4 + 2] and Decarboxylative–Mannich Sequence

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