The Behavior of Aliphatic Aldehydes in the Leuckart-Wallach Reaction

deBenneville, Peter L.; Macartney, Jane H.

doi:10.1021/ja01163a074

Cited by 61 publications

(9 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To address this issue, we conducted the infrared spectral analysis of formic acid and found a strong peak at 1726 cm –1 (SI Figure 3A) that corresponds to the CO bond stretch, showing that formic acid is present in dimer form . To check our hypothesis further, we carried out the reaction of formic acid with 2-aminoquinazolinone and obtained their infrared spectra during the reaction.…”

supporting

confidence: 75%

“…As expected, we found a shift in the peak of CO from 1726 to 1732 cm –1 in the IR spectra (SI Figure 3B). The change in peak value confirms our hypotheses that 2-aminoquinazolinone can also interact with formic acid and distort its geometry from cyclic dimer to acyclic dimer. , These results encouraged us to utilize the proton of acyclic dimer as a sophisticated hydrogen source in direct reductive amination for the synthesis of the tertiary amine from secondary amines.…”

mentioning

confidence: 99%

See 1 more Smart Citation

2-Aminoquinazolin-4(3H)-one as an Organocatalyst for the Synthesis of Tertiary Amines

et al. 2018

View full text Add to dashboard Cite

The potential of 2-aminoquinazolin-4(3H)-one as an organocatalyst for the activation of aldehydes via noncovalent interaction for the synthesis of tertiary amines using formic acid as a reducing agent is reported for the first time. The developed protocol demonstrated a dilated substrate scope for aromatic and aliphatic amines with aromatic and aliphatic aldehydes. Furthermore, the current method was also fruitful for the derivatization of ciprofloxacin and its derivative in good to excellent yields.

show abstract

supporting

confidence: 75%

mentioning

confidence: 99%

2-Aminoquinazolin-4(3H)-one as an Organocatalyst for the Synthesis of Tertiary Amines

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Leuckart-Wallach (LW) reaction is well known, which proceeds condensation of carbonyl with amines to imines and reduction with formic acid as a reducing agent. [7][8][9] As the LW reaction suffers from the high temperature (about 180 C), transition metal such as nickel, copper and metal ligand are used to overcome this drawback. 10 Although formic acid is clean and high efficient, the atom economy is poor.…”

Section: Introductionmentioning

confidence: 99%

RANEY® nickel-catalyzed reductive N-methylation of amines with paraformaldehyde: theoretical and experimental study

Luo

Qian

et al. 2014

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…For the synthesis of free 12-amino derivative of allopregnanolone, LeuckartWallach's reductive amination of 3β-acetoxy-5α-pregnane-12,20-dione 31 (20) was used (see Scheme 2): the major product 21 was a tert.butoxycarbonyl (BOC) protected 12β-amino derivative 21, which was hydrolyzed and inverted at carbon 3, yielding compounds 22 and 23,…”

Section: Resultsmentioning

confidence: 99%

Allopregnanolone and Pregnanolone Analogues Modified in the C Ring: Synthesis and Activity

et al. 2013

View full text Add to dashboard Cite

Abstract(25R)-3β-Hydroxy-5α-spirostan-12-one (hecogenin) and 11α-hydroxypregn-4-ene-3,20-dione (11α-hydroxyprogesterone) were used as starting materials for the synthesis of a series of 11-and 12-substituted derivatives of 5ξ-pregnanolone (3α-hydroxy-5α-pregnan-20-one and 3α-hydroxy-5-pregnan-20-one), the principal neurosteroid acting via γ-aminobutyric acid (GABA). These analogues were designed to study the structural requirements of the corresponding GABA A receptor. Their biological activity was measured by in vitro test with groups at the C-ring edge, rather than on specific interactions between them and the receptor.3 IntroductionAlthough steroids in general are widely understood as a class of natural products, which hold only little potential of a new breakthrough, neurosteroids are still studied with great interest (see the "Neurosteroid" copy 1,2 of Pharmacol. Ther. 2007 or recent papers [3][4][5][6] ). Unlike the family of other steroid hormones, neurosteroids do not bind to nuclear but to membrane receptors for neurotransmitters. One of the neurotransmitters -γ-aminobutyric acid (GABA) elicits the influx of chloride ions into neuronal cells, which changes the membrane potential of a given cell, which in turn prevents the transmission of subsequent neuronal signals.In agreement with this action, neurosteroids such as allopregnanolone or pregnanolone (1a and 1b, respectively, see Figure 1), 3α,5α-tetrahydrodeoxycorticosterone (2), and some of their analogues, acting via the GABA A receptor, have anxiolytic, anaesthetic, anticonvulsant, and sedative properties. 7,8 Many new types of such analogues were prepared in order to refine the knowledge of relationship between the structure of compounds and their neuronal activity.These analogues either involve compounds with additional substituents (eg., alphaxalone, 3), or have their skeleton modified by increasing 9 or decreasing 10-12 the flexibility of the molecule or even reversing its chirality. 13 Various changes were also made to the steroid side chain. [14][15][16][17] Even heteroatoms (O, N, S) were introduced into the steroid framework with varied success. 18-21Almost all the active analogues contained a hydroxyl group in position 3α. Its presence has been considered essential for the activity, even though a 3α-amino analogue, lacking the 3α-hydroxyl (i. e., 4) retained 56% of the activity of allopregnanolone. 22In our search for new analogues of allopreganolone, we prepared a number of 5-pregnane derivatives designed to exert a higher solubility in water than the principal neurosteroid 1a.The biological activity of the new products was assessed using in vitro tests, which measured 4 the binding of labelled ligands to GABA A receptors in the absence and presence of the tested compounds. In our previous paper we reported structure modification of the steroidal B ring. 11Some anomalies in the structure of the analogues were tolerated by the GABA A receptor, others not; the biological consequences of the structure modification were rationalized using...

show abstract

The Behavior of Aliphatic Aldehydes in the Leuckart-Wallach Reaction

Cited by 61 publications

References 0 publications

2-Aminoquinazolin-4(3H)-one as an Organocatalyst for the Synthesis of Tertiary Amines

2-Aminoquinazolin-4(3H)-one as an Organocatalyst for the Synthesis of Tertiary Amines

RANEY® nickel-catalyzed reductive N-methylation of amines with paraformaldehyde: theoretical and experimental study

Allopregnanolone and Pregnanolone Analogues Modified in the C Ring: Synthesis and Activity

Contact Info

Product

Resources

About