Mercury(II) Oxide/Tetrafluoroboric Acid - A New Reagent in Organic Synthesis; A Convenient Diamination of Olefins

Barluenga, José; Alonso-Cires, Luisa; Asensio, Gregorio

doi:10.1055/s-1979-28890

Cited by 77 publications

(13 citation statements)

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“…Initial studies found that treatment of alkenes with the reagent generated from tetrafluoroboric acid and mercury(I) oxide and aromatic or primary amines led to the efficient formation of 1,2-diamines 160 and Hg(0) (Scheme 36). 138 The efficiency of this process is highly dependent on the degree to which the C-Hg bond is polarized. For example, the treatment of the β-amino alkylmercury salts of acetate and halides with amines leads only to retromercuration and formation of alkenes.…”

Section: Heavy Metal-mediated Diaminationmentioning

confidence: 99%

Methods for direct alkene diamination, new & old

2012

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The 1,2-diamine moiety is a ubiquitous structural motif present in a wealth of natural products, including non-proteinogenic amino acids and numerous alkaloids, as well as in pharmaceutical agents, chiral ligands and organic reagents. The biological activity associated with many of these systems and their chemical utility in general has ensured that the development of methods for their preparation is of critical importance. While a wide range of strategies for the preparation of 1,2-diamines have been established, the diamination of alkenes offers a particularly direct and efficient means of accessing these systems. The purpose of this review is to provide an overview of all methods of direct alkene diamination, metal-mediated or otherwise.

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Section: Heavy Metal-mediated Diaminationmentioning

confidence: 99%

Methods for direct alkene diamination, new & old

2012

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“…Nitration of commercial available 9 with KNO 3 and H 2 SO 4 gave 10 , whose carbonyl group was then reduced by NaBH 4 to yield 11 . Elimination of H 2 O from 11 gave 12 , which could either be reduced to 13 or transformed into 16 [ 14 , 15 ]. Etherification of 16 with alkyl halides in the presence of KOH produced 17a and 17b .…”

Section: Chemistrymentioning

confidence: 99%

Design, Synthesis and Evaluation of Indene Derivatives as Retinoic Acid Receptor α Agonists

Guan

Luo

et al. 2016

Molecules

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A series of novel indene-derived retinoic acid receptor α (RARα) agonists have been designed and synthesized. The use of receptor binding, cell proliferation and cell differentiation assays demonstrated that most of these compounds exhibited moderate RARα binding activity and potent antiproliferative activity. In particular, 4-((3-isopropoxy-2,3-dihydro-1H-inden-5-yl)-carbamoyl)benzoic acid (36d), which showed a moderate binding affinity, exhibited a great potential to induce the differentiation of NB4 cells (68.88% at 5 μM). Importantly, our work established indene as a promising skeleton for the development of novel RARα agonists.

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“…In addition to inducing nonequivalence in the resonances of the chiral diamines, (−)-(R)-1 also proved to be an effective CSA for measuring the enantiomeric excess of sulfoximines 9a and 9b, diol 10, and tanshinone IIB 21 (11) (Items 12-15). Attempts to utilize Troeger's base (12), 26 (−)-(R)-2,2,2-trifluoro-1-(9-anthryl)ethanol [(−)-(R)-13], 1 or 2-4 as a CSA for 10 and 11 were unsuccessful. Unfortunately, 1 was not a panacea for all stubborn enantiopurity determinations.…”

Section: (−)-(R)-o-nitromandelic Acid [(−)-(R)-1]mentioning

confidence: 99%