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Search for "nitroalkanes" in Full Text gives 33 result(s) in Beilstein Journal of Organic Chemistry.
The chemistry of amine radical cations produced by visible light photoredox catalysis
Beilstein J. Org. Chem. 2013, 9, 1977–2001, doi:10.3762/bjoc.9.234
- coworkers reported a visible light-mediated aza-Henry reaction that harnesses the synthetic potential of iminium ions. Using only 1 mol % of [Ir(ppy)2(dtbbpy)](PF6) and visible light, a variety of N-aryltetrahydroisoquinolines were oxidatively coupled with nitroalkanes to provide the aza-Henry products in
- , including nitroalkanes, was shown to add to iminium ions. The authors proposed two possible mechanisms for the formation of iminium ions based on the two divergent pathways for the conversion of amine radical cations to iminium ions. The first mechanism is based on the pathway involving abstraction of a
- . König and coworkers showed that the same aza-Henry reaction can be catalyzed by the organic dye Eosin Y to afford the aza-Henry product 18 (Scheme 5) [67]. In addition to nitroalkanes, dialkyl malonates and malononitrile can be used as pronucleophiles to provide β-diester amine 19 and α-aminonitrile 20
C–C Bond formation catalyzed by natural gelatin and collagen proteins
Beilstein J. Org. Chem. 2013, 9, 1111–1118, doi:10.3762/bjoc.9.123
- 33071, Spain 10.3762/bjoc.9.123 Abstract The activity of gelatin and collagen proteins towards C–C bond formation via Henry (nitroaldol) reaction between aldehydes and nitroalkanes is demonstrated for the first time. Among other variables, protein source, physical state and chemical modification
- role in the kinetics of the nitroaldol reaction. Conclusion In conclusion, we have found that natural gelatin and collagen proteins are able to promote C–C bond formation via the Henry (nitroaldol) reaction between various aldehydes and nitroalkanes. Thus, the reaction takes place in both aqueous and
A versatile and efficient approach for the synthesis of chiral 1,3-nitroamines and 1,3-diamines via conjugate addition to new (S,E)-γ-aminated nitroalkenes derived from L-α-amino acids
Beilstein J. Org. Chem. 2013, 9, 832–837, doi:10.3762/bjoc.9.95
- derivatives by the use of chiral metal and organocatalysts [55][56]. In contrast, chiral 1,3-nitroamines, despite constituting direct precursors of chiral 1,3-diamines, are scarcely synthesized by conjugate addition of nitroalkanes to nitroalkenes. Chiral 1,3-diamines present extraordinary opportunities in
Easy and direct conversion of tosylates and mesylates into nitroalkanes
Beilstein J. Org. Chem. 2013, 9, 533–536, doi:10.3762/bjoc.9.58
- corresponding nitroalkanes, by their treatment with tetrabutylammonium nitrite (TBAN) under mild conditions. Keywords: mesylates; nitroalkanes; nucleophilic substitution; tetrabutylammonium nitrite; tosylates; Introduction Nitroalkanes have proven to be one of the most valuable, versatile classes of
- electron-withdrawing effect of the nitro group, nitroalkanes are prone to afford, under basic conditions, stabilized carbanions, which are commonly used as nucleophiles with a variety of electrophiles [8][9][10][11] leading to carbon–carbon bond formation. Furthermore, by making use of the possibility to
- transform the nitro group into other functionalities, the obtained adducts can be employed as strategic starting materials for the preparation of more complex structures [12][13]. In this context, primary nitroalkanes are the most used nitro derivatives [3][4][5][14][15][16][17], and thus, their
Reactions of salicylaldehyde and enolates or their equivalents: versatile synthetic routes to chromane derivatives
Beilstein J. Org. Chem. 2012, 8, 2166–2175, doi:10.3762/bjoc.8.244
- . The enolates and their equivalents involved in the reactions discussed in this article were derived from ketones, nitroalkanes, malononitrile and α,β-unsaturated compounds. Keywords: acetophenone; chromane; enolates; malononitrile; Michael addition; salicylaldehyde; Introduction The chromane
Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones
Beilstein J. Org. Chem. 2012, 8, 1452–1457, doi:10.3762/bjoc.8.165
- bicyclic guanidines [7][9][12]. Xiao et al. reported the addition of nitroalkanes to 4-oxo-enoates, using chiral urea derivatives [7]. Miura et al. achieved an asymmetric addition of α,α-disubstituted aldehydes to maleimides catalyzed by primary amine thiourea organocatalyst [13]. Wang et al. reported the
Continuous flow based catch and release protocol for the synthesis of α-ketoesters
Beilstein J. Org. Chem. 2009, 5, No. 23, doi:10.3762/bjoc.5.23
- allow for the complete generation of α-ketoester products in flow from the starting nitroalkanes (Scheme 3). As shown in Table 1, we demonstrate that the synthesis of the nitroolefinic esters was achieved under flow conditions in a clean and effective fashion. Moreover, this synthesis demonstrates the
A convenient synthesis of γ-functionalized cyclopentenones
Beilstein J. Org. Chem. 2005, 1, No. 11, doi:10.1186/1860-5397-1-11
- 3 in a basic medium, led to the functionalized cyclopentenones 4. Keywords: Nef reaction; conjugated addition; nitroalkanes; 1,4-diketones; functionalized cyclopentenones; Introduction The cyclopentenones are considered as an important class of compounds because they are present in a large variety
- conjugate addition of nitroalkanes to α,β-unsaturated ketones 1 leading to the nitroalkanes derivatives 2 which may be converted into their γ-diketone homologues 3 using Nef reaction. The intramolecular cyclization of 1,4-diketones 3 led to the corresponding cyclopentenones 4. Results and discussion As
- previously reported, the 1,4-addition of primary nitroalkanes [7][8][9][10][11][12] to functionalized α,β-unsaturated ketones was considered as an appropriate method to prepare multifunctional nitroketonic compounds. These intermediates are important in organic synthesis because the nitro group can be
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