476. The synthesis of alkoxy-1,2,3,4-tetrahydromaphthalene derivatives. Part I. 2-Amino-, alkylamino-, and dialkylamino-derivatives

Ames, D. E.; Evans, David P.; Grey, T. F.; Islip, P. J.; Richards, K.

doi:10.1039/jr9650002636

Cited by 23 publications

(18 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 1965, Richards and co-workers synthesized N-alkyl and N,N-dialkyl derivatives of alkoxy-1,2,3,4-tetrahydro-2-naphthylamines (Scheme 112) to start pharmacological testing. 210 Primary amines were obtained in the presence of NH 3 and Raney Ni as the catalyst. N,N-Dimethylation of the amines was carried out by the alkylation with formaldehyde in the presence of Pd/C and hydrogen.…”

Section: Use Of Several Catalysts For Reductive Aminationmentioning

confidence: 99%

See 1 more Smart Citation

Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

2020

View full text Add to dashboard Cite

The reductive amination, the reaction of an aldehyde or a ketone with ammonia or an amine in the presence of a reducing agent and often a catalyst, is an important amine synthesis and has been intensively investigated in academia and industry for a century. Besides aldehydes, ketones, or amines, starting materials have been used that can be converted into an aldehyde or ketone (for instance, carboxylic acids or organic carbonate or nitriles) or into an amine (for instance, a nitro compound) in the presence of the same reducing agent and catalyst. Mechanistically, the reaction starts with a condensation step during which the carbonyl compound reacts with ammonia or an amine, forming the corresponding imine followed by the reduction of the imine to the alkyl amine product. Many of these reduction steps require the presence of a catalyst to activate the reducing agent. The reductive amination is impressive with regard to the product scope since primary, secondary, and tertiary alkyl amines are accessible and hydrogen is the most attractive reducing agent, especially if large-scale product formation is an issue, since hydrogen is inexpensive and abundantly available. Alkyl amines are intensively produced and use fine and bulk chemicals. They are key functional groups in many pharmaceuticals, agro chemicals, or materials. In this review, we summarize the work published on reductive amination employing hydrogen as the reducing agent. No comprehensive review focusing on this subject has been published since 1948, albeit many interesting summaries dealing with one or the other aspect of reductive amination have appeared. Impressive progress in using catalysts based on earth-abundant metals, especially nanostructured heterogeneous catalysts, has been made during the early development of the field and in recent years.

show abstract

Section: Use Of Several Catalysts For Reductive Aminationmentioning

confidence: 99%

“…In 1965, Richards and co-workers synthesized N -alkyl and N , N -dialkyl derivatives of alkoxy-1,2,3,4-tetrahydro-2-naphthylamines (Scheme ) to start pharmacological testing . Primary amines were obtained in the presence of NH 3 and Raney Ni as the catalyst.…”

Section: Reductive Amination Using Heteregeneous Transition Metal Cat...mentioning

confidence: 99%

Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

2020

View full text Add to dashboard Cite

show abstract

“…Elemental analyses were performed by Atlantic Microlabs, Inc., Atlanta, GA, and the deviation was within 0.3% of the theoretical values. No-carrier-added sodium A mixture of 8-methoxy-2-tetralone (2, 2.5 g, 14.2 mmol), prepared from 1,7-dihydroxynaphthalene in two steps, 19 2-propynylamine (3.9 g, 4.9 mL, 5 equiv), and p-TsOH (150 mg, 0.8 mmol) in benzene (30 mL) was refluxed with a Dean-Stark trap for 2 h. The solvent was evaporated, and the residue was dissolved in MeOH (30 mL), to which NaCNBHg (540 mg, 8.7 mmol) was added in solid form. The solution was stirred at room temperature for 30 min and acidified with HC1 (10%) to pH -1.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of (R,S)-trans-8-hydroxy-2-[N-n-propyl-N-(3'-iodo-2'-propenyl)amino]tetralin (trans 8-OH-PIPAT): a new 5-HT1A receptor ligand

Zhuang¹,

Kung²,

Kung³

1993

J. Med. Chem.

View full text Add to dashboard Cite

In order to develop tracers with higher specific activity to supplant the currently used [3H]-8-OH-DPAT [8-hydroxy-2-(N,N-di-n-propylamino)tetralin] for in vitro and in vivo evaluation of 5-HT1A receptors, a new radioiodinated ligand was prepared. (R,S)-trans-8- Hydroxy-2-[N-n-propyl-N-(3'-iodo-2'-propenyl)amino]tetralin (trans-8-OH-PIPAT), 8, was synthesized by a 10-step reaction. Binding studies with rat hippocampal membrane homogenates showed that 8 exhibited a Ki value of 0.92 nM against (R,S)-[3H]-8-OH-DPAT. Radiolabeled [125I]-8 was prepared from the corresponding tri-n-butyltin precursor via an oxidative iododestannylation reaction with sodium [125I]iodide. Binding studies in the hippocampal homogenates revealed that [125I]-8 bound to a single high-affinity site (Kd = 0.38 +/- 0.03 nM,Bmax = 310 +/- 20 fmol/mg of protein). Competition binding experiments clearly indicated that the new ligand displayed the expected 5-HT1A receptor binding profile. The rank order of potency was (R,S)-trans-8-OH-PIPAT > (R,S)- 8-OH-DPAT > WB4101 > 5-HT > (R,S)-trans-7-OH-PIPAT > (R,S)-7-OH-DPAT > (R,S)-propranolol > spiperone >> ketanserin >> dopamine > atropine. This new ligand offers several unique advantages, including high specific activity, high binding affinity, and low nonspecific binding, all of which make it an excellent probe for the investigation and characterization of 5-HT1A receptors.

show abstract

“…The reaction was increased to rt and and stirred for 4 h. The reaction mixture was washed with HCl (0.1 M; 3 × 10 mL) and NaOH (0.05 M, 3 × 10 mL). The organic phase was then dried (MgSO 4 ) and concentrated under vacuum to afford the titled compound [43] (112 mg, 89%).…”

Section: (2s)-n-(8-methoxy-1234-tetrahydronaphthalen-2-yl)-n-propylpr...mentioning

confidence: 99%

Stereoselective Transaminase‐Mediated Synthesis of Serotonin and Melatonin Receptor Agonists

et al. 2022

View full text Add to dashboard Cite

Transaminase enzymes have significant potential for the stereoselective synthesis of drugs or drug precursors. Here, starting from one prochiral β‐tetralone, a short and efficient chemoenzymatic synthesis of four agonists of the serotonin/melatonin receptors have been developed. The key step is the stereoselective transamination of the prochiral ketone to produce both enantiomers of 8‐methoxy‐2‐aminotetraline in high yields and enantiomeric excesses. This was followed by either amidation to give the 8‐methoxy‐2‐acetimidotetralines or several facile chemical steps to the 8‐hydroxy‐2‐aminodipropyltetralines.

show abstract

476. The synthesis of alkoxy-1,2,3,4-tetrahydromaphthalene derivatives. Part I. 2-Amino-, alkylamino-, and dialkylamino-derivatives

Cited by 23 publications

References 0 publications

Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

Synthesis of (R,S)-trans-8-hydroxy-2-[N-n-propyl-N-(3'-iodo-2'-propenyl)amino]tetralin (trans 8-OH-PIPAT): a new 5-HT1A receptor ligand

Stereoselective Transaminase‐Mediated Synthesis of Serotonin and Melatonin Receptor Agonists

Contact Info

Product

Resources

About