A Safe and Efficient Method for Preparation of N,N'-Unsymmetrically Disubstituted Ureas Utilizing Triphosgene

Majer, Pavel; Randad, Ramnarayan S.

doi:10.1021/jo00086a061

Cited by 200 publications

(105 citation statements)

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“…However, numerous reports were found in the literature associated to the synthesis of symmetrical/unsymmetrical urea and thiourea derivatives individually using different surrogates like phosgene/thiophosgene, 5 isocyanates/isothiocyanates, 6 CS 2 /CO 2 , 7 dithiocarbamates, 8 and carbonylimidazoles. 9 The usage of phosgene/thiophosgene is most traditional path for the synthesis of urea and thioureas.…”

Section: Figure 1some Biologically Active Urea and Thiourea Derivatimentioning

confidence: 99%

Unsymmetrical urea and thiourea derivatives: An efficient nano BF 3-SiO 2 catalyzed PEG-400 mediated sonochemical synthesis and biological evaluation

Janakiramudu¹,

Rao²,

Madhu³

et al. 2017

Org. Commun.

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An efficient and green approach has been developed for the synthesis of (substituted phenyl)-3-(4-(4-nitrophenylthio)phenyl)urea/thiourea derivatives 6(a-j) using non-hazardous green solvent, PEG-400 under ultrasound irradiation conditions in the presence of a reusable silica-supported Lewis acid catalyst, nano-BF 3 -SiO 2 via simple addition reaction of 4-(4-nitrophenylthio)aniline (4) with substituted phenyl isocyanates/isothiocyanates 5 (a-j). The advantages of developed method are convenient, offered higher yield of products with purity, less reaction time, easy work-up and reusability of the catalyst. Structures of the title products were established by IR, NMR ( 1 H, 13 C), mass spectral data and elemental analysis. Antimicrobial activity of the newly synthesized compounds was tested and the bio-screening data disclosed that urea derivatives, 6a and 6d, and thiourea derivatives, 6f, 6i and 6j showed potential antimicrobial activity against the growth of selected microorganisms.

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Section: Figure 1some Biologically Active Urea and Thiourea Derivatimentioning

confidence: 99%

Unsymmetrical urea and thiourea derivatives: An efficient nano BF 3-SiO 2 catalyzed PEG-400 mediated sonochemical synthesis and biological evaluation

Janakiramudu¹,

Rao²,

Madhu³

et al. 2017

Org. Commun.

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“…Synthesis of linear carbonates mainly makes use phosgene and its derivatives [11][12][13][14] as the starting material, while cyclic carbonates are synthesized from propylene oxide. As an alternative approach, substituted chloroformates [15][16][17] are the most frequently used reagents for the preparation of organic carbonates.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectroscopic Investigation and Computational Studies of 2-Formyl-4-(Phenyldiazenyl)Phenyl Methyl Carbonate and 4-((4-Chlorophenyl)Diazenyl)-2-Formylphenyl Methyl Carbonate

Arokiasamy

Manikandan

Thanikachalam

et al. 2016

ILCPA

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ABSTRACT. Two new compounds namely 2-formyl-4-(phenyldiazenyl)phenyl methyl carbonate (FPMC) and 4-((4-chlorophenyl) diazenyl)-2-formylphenyl methyl carbonate (CFPMC) have been synthesized and have characterized using FT-IR, FT-Raman, 1 H and 13 C NMR techniques. Computational optimization studies have been carried out using Hatree-Fock (HF) and Density Functional Theory (DFT-B3LYP) methods with 6-31+G(d, p) basis set of Gaussian 09W software. The stable configuration of the title compounds were achieved theoretically by potential energy surface scan analysis. The complete vibrational assignments were performed on the basis of total energy distribution (TED) and natural bonding orbital (NBO) have been studied. Various parameters such as E HOMO , E LUMO , total energy, dipole moment, polarizability, first order hyperpolarizability, zero-point vibrational energy as well as thermal properties were analyzed and reported for the title compounds.

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“…From the environmental point of view, other synthetic methods for the synthesis of carbamates have many disadvantages [4][5][6][7] as shown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Carbamoylation of primary, secondary and aromatic amines by dimethyl carbonate in a flow system over solid catalysts

Litwinowicz

Kijeński

2015

sustain chem process

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Background: Carbamate esters represent an important class of organic compounds which find wide application in chemical industry. Classical procedures for the preparation of carbamates are based on the reaction with a very risky compound -phosgene or phosgene derivatives. Results: A phosgene-free flow-system synthesis of eight carbamates in the reaction of various amines with dimethyl carbonate has been presented. The influence of amine order and structure on their activity in the carbamoylation process was studied. Fe 2 O 3 , Fe 2 O 3 /SiO 2 , Fe 2 O 3 /CoO/NiO/SiO 2 , TZC-3/1 and T-4419 were used as catalysts for the process.

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A Safe and Efficient Method for Preparation of N,N'-Unsymmetrically Disubstituted Ureas Utilizing Triphosgene

Cited by 200 publications

References 0 publications

Unsymmetrical urea and thiourea derivatives: An efficient nano BF 3-SiO 2 catalyzed PEG-400 mediated sonochemical synthesis and biological evaluation

Unsymmetrical urea and thiourea derivatives: An efficient nano BF 3-SiO 2 catalyzed PEG-400 mediated sonochemical synthesis and biological evaluation

Synthesis, Spectroscopic Investigation and Computational Studies of 2-Formyl-4-(Phenyldiazenyl)Phenyl Methyl Carbonate and 4-((4-Chlorophenyl)Diazenyl)-2-Formylphenyl Methyl Carbonate

Carbamoylation of primary, secondary and aromatic amines by dimethyl carbonate in a flow system over solid catalysts

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