Organic reaction in water. Part 4. New synthesis of vicinal diamines using zinc powder-promoted carbon–carbon bond formation

Tsukinoki, Takehito; Nagashima, Shigeru; Mitoma, Yoshiharu; Tashiro, Masashi

doi:10.1039/b001533o

Cited by 53 publications

(19 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, all these methods are highly moisture‐sensitive and troublesome to operate. Recently, Tsukinoki et al reported a coupling of imines in water to give diamines in good yields (Scheme 7) (29). The reaction proceeded smoothly in water in the presence of zinc powder and NH 4 Cl or l ‐Tyr to give the diamines in good chemical yields.…”

Section: Exploiting the Synthetic Chemistry Of Vicinal Diamine Functimentioning

confidence: 99%

Vicinal Diamino Functionalities as Privileged Structural Elements in Biologically Active Compounds and Exploitation of their Synthetic Chemistry

2006

View full text Add to dashboard Cite

show abstract

Section: Exploiting the Synthetic Chemistry Of Vicinal Diamine Functimentioning

confidence: 99%

Vicinal Diamino Functionalities as Privileged Structural Elements in Biologically Active Compounds and Exploitation of their Synthetic Chemistry

2006

View full text Add to dashboard Cite

show abstract

“…[62][63][64][65][66] Water is the solvent of choice not only from an environmental standpoint, but also from an economic point of view since it is cheap, nonflammable, and abundantly available. [67][68][69][70] Water behaves differently from other commonly 4 used organic solvents in terms of its unique and unusual physical properties, such as high surface tension, high dielectric constant, high specific heat, large cohesive energy density and also chemical properties, particularly its amphoteric nature and the ability to form hydrogen bonds. 71,72 Moreover, hydrophobic interactions offered by water molecules with organic reactants sometimes facilitate certain organic processes.…”

Section: Introductionmentioning

confidence: 99%

Room Temperature One-Pot Green Synthesis of Coumarin-3-carboxylic Acids in Water: A Practical Method for the Large-Scale Synthesis

Brahmachari

2015

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

A simple, facile and convenient practical method for the room temperature one-pot synthesis of a series of potentially biologically active coumarin-3-carboxylic acids has been developed in water from the Knoevenagel condensation and intramolecular cyclization of diverse 2hydroxybenzaldehydes with Meldrum's acid using either potassium carbonate or sodium azide as commercially available, cheap and eco-friendly catalyst. The salient features of the present protocol are mild reaction conditions, good to excellent yields, high atom-economy, environmentally benignity, easy isolation of products, without column chromatography, clean reaction profiles and applicability towards large-scale synthesis.General. Infrared spectra were recorded using a Shimadzu (FT-IR 8400S) FT-IR spectrophotometer using KBr disc. 1 H and 13 C NMR spectra were obtained at 400 MHz and 100 MHz respectively, using Bruker DRX-400 spectrometer and DMSO-d 6 as the solvent.Mass spectra (TOF-MS) were measured on a QTOF Micro mass spectrometer. Elemental analyses were performed with an Elementar Vario EL III Carlo Erba 1108 micro-analyzer instrument. X-ray data were collected on a Bruker single crystal X-ray difractometer (model:APEX 2). Melting point was recorded on a Chemiline CL-726 melting point apparatus and is uncorrected. Thin Layer Chromatography (TLC) was performed using silica gel 60 F 254 (Merck) plates. General procedure for the synthesis of coumarin-3-carboxylic acids (3): An oven-driedscrew cap test tube was first charged with a magnetic stir bar, salicylaldehydes (1, 1.0 mmol), Meldrum's acid (2, 1.0 mmol; 144 mg), distilled water (5 mL) and K 2 CO 3 (20 mol%; 28 mg).The whole mixture was then stirred vigorously at room temperature (24-26 ο C) for 20 h to complete the conversion. Upon completion, the resulting solution was acidified with chilled acid-water, when solid mass precipitated out, filtered off and thoroughly washed with water to obtain almost pure product of coumarin-3-carboxylic acids 3. For further purification, the products were crystallized from ethyl acetate. All the products 3 were also synthesized repeating the same reaction using sodium azide (50 mol%; 33 mg) as the catalyst in place of potassium carbonate. The structure of each purified product was confirmed by its analytical as well as spectral studies including FT-IR, 1 H NMR, 13 C NMR and TOF-MS. For few entries, 2D-NMR ( 1 H-1 H COSY, HMQC and HMBC) spectral properties were also studied.In addition, single X-ray crystallographic studies for one entry, 6-methoxycoumarin-3carboxylic acid (3f), was performed.

show abstract

“…They performed the reductive coupling of aromatic imines by the use of zinc powder and additives such as NH4Cl and 1-tyrosine in water without any organic solvents under mild conditions to give the corresponding vicinal diamines in good yields. Similarly, cross coupling of N-benzylideneaniline and benzaldehyde proceeds in aqueous media to afford the corresponding 2-aminoalcohol [148,149]. On the other hand, highly meso-diastereoselective pinacol coupling of aromatic aldehydes mediated by aluminium powder/copper sulphate in water under reflux conditions is known [150].…”

Section: %mentioning

confidence: 99%

A Review on the Recent Advances in the Reductions of Carbon–Carbon/Oxygen Multiple Bonds Including Aromatic Rings Using Raney Ni–Al Alloy or Al Powder in the Presence of Noble Metal Catalysts in Water

et al. 2018

View full text Add to dashboard Cite

Over the last few years, heterogeneous catalysts have attracted much attention with a view to lowering reaction temperatures and improving the selectivity of many organic syntheses. When designing or optimizing a catalyst, attention is devoted to the nature of the active sites, and how they interact with the reactants, intermediates and products of the catalytic process. It has become clear that the structural and electronic features of an active site are usually affected by the chemical environment in which it operates. Raney Ni-Al alloy and noble metal catalysts such as Ru/C, Rh/C, Pd/C and Pt/C are employed in the selective and complete hydrogenation of various functional groups and aromatic rings in presence of water in a sealed tube. Al powder was found to be capable of reducing a carbonyl group, an alkyne group and the aromatic ring of biphenyl, fluorene, 9,10-dihydroanthracene, polyarenes and N-heterocycles using noble metal catalysts in water under mild reaction conditions.

show abstract

Organic reaction in water. Part 4. New synthesis of vicinal diamines using zinc powder-promoted carbon–carbon bond formation

Cited by 53 publications

References 14 publications

Vicinal Diamino Functionalities as Privileged Structural Elements in Biologically Active Compounds and Exploitation of their Synthetic Chemistry

Vicinal Diamino Functionalities as Privileged Structural Elements in Biologically Active Compounds and Exploitation of their Synthetic Chemistry

Room Temperature One-Pot Green Synthesis of Coumarin-3-carboxylic Acids in Water: A Practical Method for the Large-Scale Synthesis

A Review on the Recent Advances in the Reductions of Carbon–Carbon/Oxygen Multiple Bonds Including Aromatic Rings Using Raney Ni–Al Alloy or Al Powder in the Presence of Noble Metal Catalysts in Water

Contact Info

Product

Resources

About