Enaminouraciles as Precursors for Synthesis of Pyrimido[4,5-a]pyrimidine- 2,4-diones

2000 ◽  
Vol 55 (5) ◽  
pp. 443-447 ◽  
Author(s):  
W. S. Hamama
Keyword(s):  
Mannich Reaction ◽  
Aromatic Amines ◽  
Room Temperature ◽  
Secondary Amines

The reaction of 6-aminouracil 1 with formaldehyde and secondary amines in ethanol at room temperature gave the corresponding 5-alkylaminomethyl derivatives (2a-c) and bis(4- pyrimidyl) methane (4). Also, Mannich reaction with primary aliphatic and aromatic amines at room temperature afforded pyrimid[4,5-d]pyrimidine (5 and 6). Treatment of 1 with o-phenylenediamine through transamination gave com pound 7 which cyclized through intramolecular Mannich reaction with formalin to yield pyrimido[4,5-e]-[l,4]diazepine (8).

A Convenient One-Pot Synthesis of Pyrazolo[3,4-d]pyrimidines and s-Triazolo[3,4-b][1,3,5]thiadiazines

1997 ◽  
Vol 52 (11) ◽  
pp. 1401-1412 ◽  
Author(s):  
Zeinab A. Hozien ◽  
Abd El-Wareth A. O. Sarhan ◽  
Hassan A. H. El-Sherief ◽  
Abdalla M. Mahmoud
Keyword(s):  
Mannich Reaction ◽  
Aromatic Amines ◽  
Good Yield ◽  
Room Temperature ◽  
Secondary Amines ◽  
One Pot ◽  
Aminomethyl Derivatives ◽  
Primary Aromatic Amines ◽  
The Mannich Reaction ◽  
Primary Aliphatic Amines

Abstract The reaction of 5-amino-3-aryl-1-phenylpyrazoles (1a-d) with formaldehyde and secondary amines in boiling ethanol gave the corresponding 4-alkylaminomethyl derivatives (2a-f) and bis-(4-pyrazolyl)methane (4a,b) as byproduct. Such reaction with primary aliphatic and aro­ matic amines at room temperature afforded 1,3,5-trisubstituted (5a-h) and 1,3.5,7-tetrasubstituted tetrahydropyrazolo[3,4-d]pyrimidines (8a-k) respectively in good yield. Similarily, the Mannich reaction of 5-mercapto-3-phenyl-1,2,4-triazole (9) with secondary amines, in boiling ethanol, and primary aromatic amines, at room temperature, gave 2 -substituted aminomethyl derivatives (10a-c) and (14a-g) respectively,while with primary aliphatic amines, p-toluidine and p-anisidine,at room temperature,and with other primary aromatic amines, in boiling ethanol, afforded the cyclized products 12,4-triazolo[3,4-b]thiadiazines (13a-e); (15f,g) and (15a-e), respectively.

Ultrasound-assisted rapid synthesis of β-aminoketones with direct-type catalytic Mannich reaction using bismuth(III) triflate in aqueous media at room temperature

2012 ◽  
Vol 66 (1) ◽  
Author(s):  
S. Ozturkcan ◽  
Kadir Turhan ◽  
Zuhal Turgut
Keyword(s):  
Reaction Time ◽  
Mannich Reaction ◽  
Aromatic Amines ◽  
Room Temperature ◽  
Aqueous Media ◽  
Aromatic Aldehydes ◽  
Rapid Synthesis ◽  
Low Toxicity ◽  
Ultrasound Assisted ◽  
Easy Operation

AbstractAn innovative, powerful, efficient and relatively rapid method was developed to synthesise various β-aminoketone derivatives from cyclohexanone, substituted aromatic amines and aromatic or hetero-aromatic aldehydes via ultrasound-assisted direct-type catalytic Mannich reaction using bismuth(III) triflate in water. Good yields of the desired β-aminoketones were obtained at room temperature by ultrasound-assisted reaction within 1–2 h. The major advantages of the proposed method are undemanding conditions, easy operation, low toxicity, shorter reaction time, anti selectivity and higher yields in comparison with conventional methods.

One-pot three-component Mannich reaction in water catalyzed by eco-friendly, hydrophobic and recyclable sulfonic acid based nanosilica (SBA-15-Ph-PrSO3H)

RSC Advances ◽  
2014 ◽  
Vol 4 (71) ◽  
pp. 37941-37946 ◽  
Author(s):  
Daryoush Zareyee ◽  
Hamidreza Alizadeh
Keyword(s):  
Mannich Reaction ◽  
Aromatic Amines ◽  
Sulfonic Acid ◽  
Room Temperature ◽  
Aromatic Aldehydes ◽  
Green Method ◽  
One Pot ◽  
The Mannich Reaction ◽  
Reaction In Water

A mild, effective and green method for the Mannich reaction of aromatic aldehydes, aromatic amines and ketones has been accomplished in good to excellent yields using hydrophobic SBA-15-Ph-PrSO3H in water at room temperature.

Hydrosilylation and Mukaiyama Aldol-type Reactions of Imine and Quinoline Derivatives Catalyzed by a Mesoionic Carbene-Stabilized Borenium Ion

2021 ◽  
Author(s):  
Joshua J. Clarke ◽  
Karthik Devaraj ◽  
Brian Bestvater ◽  
Ryoto Kojima ◽  
Patrick Eisenberger ◽  
...  
Keyword(s):  
Room Temperature ◽  
Secondary Amines ◽  
Catalyst Loading ◽  
Quinoline Derivatives ◽  
Mukaiyama Aldol

Aldimines and ketimines containing electron-donating and electron-withdrawing groups can be hydrosilylated with borenium catalysts at as low as 1 mol% catalyst loading at room temperature, providing the corresponding secondary amines...

scholarly journals Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles

2020 ◽  
Vol 2020 ◽  
pp. 1-9
Author(s):  
Hassan Kabirifard ◽  
Pardis Hafez Taghva ◽  
Hossein Teimouri ◽  
Niloofar Koosheshi ◽  
Parastoo Javadpour ◽  
...  
Keyword(s):  
High Temperature ◽  
Carbonyl Group ◽  
Aromatic Amines ◽  
Room Temperature ◽  
Organic Ligands ◽  
Carboxyl Group ◽  
Primary Aromatic Amines

The reaction of 4-benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione (1) with aminoheteroaryls, lamotrigine, 1,3-diaminoheteroaryls, dapsone, NH2R (hydroxylamine, DL-1-phenylethylamine, and metformin), and 4,4′-bipyridine in THF/H2O (1 : 1) at room temperature led to 3-N-phenylthiocarbamoyl-2-butenamides 2–5, while that with naphthylamines and 1,3-phenylenediamine in ethanol at high temperature led to 5-phenylamino-2,5-dihydrothiophene-2-ones 6–8 as organic ligands in the medium to good yields. These showed the nucleophilic attacks of N-nucleophiles, except primary aromatic amines, on thioester carboxyl group (C-2) of thiophene-2,3-dione ring 1. However, the nucleophilic attacks of primary aromatic amines on the carbonyl group (C-3) of thiophene-2,3-dione 1 occurred in the form of substituted thiophenes.

Alkene Difunctionalization Directed by Free Amines: Diamine Synthesis via Nickel-Catalyzed 1,2-Carboamination

2021 ◽  
Author(s):  
Taeho Kang ◽  
José Manuel González ◽  
Zi-Qi Li ◽  
Klement Foo ◽  
Peter Cheng ◽  
...  
Keyword(s):  
Nickel Catalyst ◽  
Room Temperature ◽  
Kinetic Studies ◽  
Fine Tuning ◽  
Secondary Amines ◽  
Protecting Group ◽  
Wide Range ◽  
Leaving Group ◽  
Primary And Secondary Amines ◽  
Reaction Proceeds

A versatile method to access differentially substituted 1,3- and 1,4-diamines via a nickel-catalyzed three-component 1,2-carboamination of alkenyl amines with aryl/alkenylboronic ester nucleophiles and N–O electrophiles is reported. The reaction proceeds efficiently with free primary and secondary amines without needing a directing auxiliary or protecting group, and is enabled by fine-tuning the leaving group on the N–O reagent. The transformation is highly regioselective and compatible with a wide range of coupling partners and alkenyl amine substrates, all performed at room temperature. A series of kinetic studies support a mechanism in which alkene coordination to the nickel catalyst is turnover-limiting.

scholarly journals Mannich reaction of dihydropyridine derivatives I. Reactions with secondary amines.

1980 ◽  
Vol 28 (11) ◽  
pp. 3163-3171 ◽  
Author(s):  
JIRO ARITOMI ◽  
SHOZO UEDA ◽  
HARUKI NISHIMURA
Keyword(s):  
Mannich Reaction ◽  
Secondary Amines ◽  
Dihydropyridine Derivatives

The Mannich Reaction Between Aromatic Ketones, Aromatic Aldehydes and Aromatic Amines

Synthesis ◽  
1991 ◽  
Vol 1991 (09) ◽  
pp. 717-718 ◽  
Author(s):  
Yi Lin ◽  
Lei Huangshu ◽  
Zou Junhua ◽  
Xu Xiujuan
Keyword(s):  
Mannich Reaction ◽  
Aromatic Amines ◽  
Aromatic Aldehydes ◽  
Aromatic Ketones ◽  
The Mannich Reaction
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