Novel Direct Synthesis of Asymmetrical Urea Compounds from Trichloroethyl Carbamates Using Catalytic DBU

Jang, Ho Seong; Kim, Hee‐Kwon

doi:10.1002/bkcs.11314

Cited by 5 publications

(3 citation statements)

References 21 publications

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“…This suggests that the mechanism for this reaction is that methylamine nucleophilic attacks the isothiocyanate intermediate (yielded by the well-known base-promoted elimination of trichloroethanol) to produce the corresponding urea compounds (Azad et al, 2006). Review of previous literature, we found that the occurrence of this reaction required high pressure (Azad et al, 2006), high temperature (Jeong et al, 2016), or catalyst (Simard et al, 2009; Kono et al, 2013; Jang and Kim, 2017; Zhang et al, 2018) conditions. Accordingly, a new and more practical approach for the synthesis of ureido glycosides at room temperature and normal pressure without catalyst is reported here.…”

Section: Resultsmentioning

confidence: 78%

Design and Optimization of Thioglycosyl–naphthalimides as Efficient Inhibitors Against Human O-GlcNAcase

et al. 2019

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β-N-acetylhexosaminidases represent an important class of exoglycosidases and have emerged as the promising targets for drug and pesticide discovery. Among these, human O-GlcNAcase (hOGA) has been reported to be closely linked to several diseases such as Alzheimer's disease, diabetes, and cancer. Potent hOGA inhibitors with high selectivity are therefore of great significance for the regulation of the corresponding physiological processes. In this study, several classes of novel and readily available thioglycosyl-naphthalimides bearing the amide linker were designed and synthesized. To investigate their potency and selectivity, the inhibitory efficiencies toward hOGA and human β-N-acetylhexosaminidase B (HsHexB) were assayed. Especially, compounds 10a ( K i = 0.61 μM) and 16l ( K i = 0.72 μM) exhibited excellent inhibitory potency against hOGA and high selectivity (HsHexB, K i > 100 μM). In addition, during the preparation of these thioglycosyl–naphthalimides, a new practical method was developed for the synthesis of ureido glycosides from trichloroethyl carbamates at room temperature and normal pressure without catalyst. Furthermore, the possible binding modes of hOGA with 10a , 10d , and 16j were studied using molecular docking and molecular dynamics simulations to explore the molecular basis for the potency of these thioglycosides. This work present here provides useful clues for the further structural optimization toward hOGA.

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Section: Resultsmentioning

confidence: 78%

Design and Optimization of Thioglycosyl–naphthalimides as Efficient Inhibitors Against Human O-GlcNAcase

et al. 2019

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“…We also reported a new synthesis of ureas from N-Troc-protected amines by using DBU, and syntheses of ureas from Alloc, Troc, and Cbz carbamates by using CaI 2 . 41,42 However, conversion yields from Troc carbamates to ureas in the presence of DBU were not high, and the reactions using CaI 2 had to be carried out at 80 °C. We were therefore interested in discovering an effective conversion of carbamates into ureas by using novel metal catalysts, such as metal trifluoromethanesulfonates (triflates).…”

Section: Syn Lettmentioning

confidence: 99%

Lanthanum(III) Trifluoromethanesulfonate Catalyzed Direct Synthesis of Ureas from N-Benzyloxycarbonyl-, N-Allyloxycarbonyl-, and N-2,2,2-Trichloroethoxycarbonyl-Protected Amines

Bui

Kim

2020

Synlett

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A novel lanthanum triflate mediated conversion of N-benzyloxycarbonyl-, N-allyloxycarbonyl-, and N-trichloroethoxycarbonyl-protected amines into nonsymmetric ureas was discovered. In this study, lanthanum triflate was found to be an effective catalyst for preparing various nonsymmetric ureas from protected amines. A variety of protected aromatic and aliphatic carbamates reacted readily with various amines in the presence of lanthanum triflate to generate the desired ureas in high yields. This result demonstrated that this novel lanthanum triflate catalyzed preparation of ureas from Cbz, Alloc, and Troc carbamates can be employed for the formation of various urea structures.

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“…Nowadays, organocatalysts and are considered as commercially available alternatives for urea synthesis [55,60,61] . 1,8‐Diazabicyclo(5.4.0)undec‐7‐ene ( DBU ), an amidine‐based compound is known for its catalytic reactivity for urea synthesis, [58,62] in the fixation of CO 2 by alcohols [63,64] or epoxides [65,66] providing the cyclic carbonates (CCs) and in many other reactions [67–69] . Moreover, guanidine‐ and thiourea‐based catalysts afford activation of the carbonyl group through hydrogen bonding [58,70–72] .…”

Section: Introductionmentioning

confidence: 99%

Green Microwave‐Assisted Synthesis of Cyclic/Acyclic Ureas from Propylene Carbonate

et al. 2022

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Herein, an organocatalyzed synthetic pathway for the preparation of (a)cyclic ureas from their parent primary aliphatic or aromatic mono‐/diamines with propylene carbonate (PC) as a carbonylating agent (CAT) obtaining reasonable to very good yields with high selectivity. Our method is considered green as nine out of twelve green chemistry principles (GCPs) are fulfilled. Most importantly, the absence of solvent, energy‐efficient pathway, in addition to the ease of synthesis and separation, under fast reaction times down to a few minutes together with the straightforward workup with minimum use of organic solvents. Our method was successful in preparing 1,3‐diphenylurea from aniline giving 8 % yield in 10 minutes, to our knowledge, this was not previously reported using aromatic amines with carbonate esters. The prepared compounds were fully characterized by spectroscopic and thermal techniques. The method is applicable for primary rather than secondary amines, which implies high chemoselectivity of the former for the synthesis of urea compounds.

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Novel Direct Synthesis of Asymmetrical Urea Compounds from Trichloroethyl Carbamates Using Catalytic DBU

Cited by 5 publications

References 21 publications

Design and Optimization of Thioglycosyl–naphthalimides as Efficient Inhibitors Against Human O-GlcNAcase

Design and Optimization of Thioglycosyl–naphthalimides as Efficient Inhibitors Against Human O-GlcNAcase

Lanthanum(III) Trifluoromethanesulfonate Catalyzed Direct Synthesis of Ureas from N-Benzyloxycarbonyl-, N-Allyloxycarbonyl-, and N-2,2,2-Trichloroethoxycarbonyl-Protected Amines

Green Microwave‐Assisted Synthesis of Cyclic/Acyclic Ureas from Propylene Carbonate

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