Synthesis of methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates and their reactions with amines and amidines

Kornienko, A. N.; Пильо, С. Г.; Прокопенко, В. М.; Броварец, В. С.

doi:10.1134/s1070363214080210

Cited by 6 publications

(8 citation statements)

References 21 publications

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“…Methyl 5‐((5‐amino‐3‐1 H ‐pyrazol‐1‐yl)sulfonyl)‐1,3‐oxazole‐4‐carboxylates 24, 25 were prepared by refluxing of methyl 5‐chlorosulfonyl‐2‐phenyl‐1,3‐oxazole‐4‐carboxylate ( 23 ) with 3‐methyl‐ or 3‐phenyl‐1 H ‐pyrazol‐5‐amine and triethylamine in dioxane (Scheme ) …”

Section: Resultsmentioning

confidence: 99%

“…4‐Cyano‐2‐(4‐methylphenyl)‐1,3‐oxazole‐5‐sulfonyl chloride ( 17 ) and 4‐cyano‐2‐phenyl‐1,3‐oxazole‐5‐sulfonyl chloride ( 18 ) were synthesized previously from appropriate enamide 1 or 2 . Methyl 5‐chlorosulfonyl‐2‐phenyl‐1,3‐oxazole‐4‐carboxylate ( 24 ) have been synthesized by the method described in the literature …”

Section: Methodsmentioning

confidence: 99%

“…Reagents and conditions: (a) 2-(methylamino)ethanol, Et 3 N, THF, rt, 12 hours; (b) 2-(4-chlorophenyl)-2-piperidin-1-ylethanamine, Et 3 N, THF, rt, 12 hours; (c) arenethiol, Et 3 N, acetonitrile, rt, 8 hours; Ag 2 CO 3 , acetonitrile, reflux, 8 to 10 hours; (d) H 2 O 2 , AcOH, reflux, 1 hour of methyl 5-chlorosulfonyl-2-phenyl-1,3-oxazole-4-carboxylate (23) with 3-methyl-or 3-phenyl-1H-pyrazol-5amine and triethylamine in dioxane (Scheme 3). [48] Data of synthesized novel 1,3-oxazole derivatives are presented in Section 4. NMR ( 1 H and 13 C NMR), chromato-mass, and elemental analysis confirm reliably the structure of the obtained compounds.…”

Section: Chemistrymentioning

confidence: 99%

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Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Kachaeva

Hodyna

Obernikhina

et al. 2019

Journal of Heterocyclic Chem

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A series of new 1,3‐oxazole derivatives, containing in position 5 both donor and acceptor substituents were synthesized. These substances were considered as potentially active anticancer pharmacophores in the human tumor cell line panel derived from nine cancer types, including lung, colon, melanoma, renal, ovarian, brain, leukemia, breast, and prostate. Primary in vitro one‐dose anticancer screening was shown that compounds with acceptor substituents (such as –C(O)OMe, –CN) in the position 5 inhibit the growth of most cell lines, and compounds with donor substituents (such as –NHR, −SR) in the position 5 do not practically inhibit the growth of cancer cell lines. It can be assumed that the pharmacological activity of 1,3‐oxazole derivatives depends on donor/acceptor nature of the substituents in position 5. It was proposed to evaluate the donor/acceptor ability of 1,3‐oxazole derivatives using the special parameter φ0, which takes into account the relative position of the boundary levels (HOMO end LUMO). The quantum‐chemical modeling was performed; the special parameter φ0 for 1,3‐oxazole derivatives correlates with the experimental results. Quantum‐chemical calculations of the special parameter φ0 allow modeling the pharmacological activity of 1,3‐oxazole derivatives by introducing donor or acceptor substituents at position 2 or 5. This work may be useful for chemists to develop a target synthesis of potential biologically active compounds.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

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Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Kachaeva

Hodyna

Obernikhina

et al. 2019

Journal of Heterocyclic Chem

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“…Treatment with triphenylphosphine, hexachloroethane and triethylamine produced iminophosphorane 184 in good yield. [40,41] The Cornforth rearrangement is a reaction which is specific for 4-acyloxazoles. Annulation of pyrimidine rings to 4-carboxy-5-aminooxazoles using a variety of one-carbon synthons.…”

Section: Starting From Various Other 245-trisubstituted Oxazolesmentioning

confidence: 99%

“…When these hemi-aminals were heated to 110-140°C, ring closure to the oxazolopyrimidines 10 was observed, but also ring opening to the ester and the amide. [40,41] Eur. The desired oxazolo[4,5-d]pyrimidines 10 were still only obtained in low yields.…”

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confidence: 99%

Synthesis and Biological Activity of Oxazolopyrimidines

et al. 2018

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In this work, the synthesis of oxazolo[4,5‐d]pyrimidines and oxazolo[5,4‐d]pyrimidines is reviewed. The review is focused on the construction of the scaffold rather than on its further modification. Nevertheless, selected examples illustrate some of the most common modifications of these scaffolds. The synthetic part is complemented by an overview of their biological activity. This review covers literature and patents from 1967 until the present.

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Recent advances in the synthesis and applications of oxazolo[5,4-d]pyrimidines (microreview)

Mieczkowski

Bieszczad

2016

Chem Heterocycl Comp

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Synthesis of methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates and their reactions with amines and amidines

Abstract: Previously unknown methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates have been synthesized. Their reactions with amines and amidines have yielded the corresponding sulfonamides and 6H,7H-[1,3]oxazolo-[5,4-d]pyrimidin-7-ones.

Cited by 6 publications

References 21 publications

Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Synthesis and Biological Activity of Oxazolopyrimidines

Recent advances in the synthesis and applications of oxazolo[5,4-d]pyrimidines (microreview)

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