- A 2 - substituted oxazoline or 2 - substituted piperazine synthetic method (by machine translation)
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The invention discloses a method for synthesizing 2 - substituted oxazoline or 2 - substituted oxazine new method, by nitrile and amino ethanol or 3 - amino - 1 - propanol as raw material, in the absence of solvent, can be used for the recycling of the sulfur to induce synthesis of 2 - substituted oxazoline and 2 - substituted piperazine. The method of the invention has low cost, simple reaction process, mild reaction conditions, the reaction time is short, the yield and the like, is suitable for the industrial generation. (by machine translation)
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Paragraph 0038; 0050
(2017/08/25)
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- Synthesis and pharmacological evaluation of benzamide derivatives as potent and selective sigma-1 protein ligands
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A series of novel benzamide-derived compounds was designed, synthesized and pharmacologically evaluated. Among all 37 synthesized compounds, two series were developed with the modulation of the nature, the position of atoms or groups on the benzamide scaffold, but also the nature of the amine group separated from the benzamide with 2, 3 or 4 methylene groups. In vitro competition binding assays against sigma proteins (sigma-1 S1R and sigma-2 S2R) revealed that most of them conferred S2R/S1R selectivity toward without cytotoxic effects on SY5Y cells, especially with the first series with compounds 7a-z. Some selected compounds were also evaluated for their agonist and antagonist activities on a panel of 40 receptors. Results showed the importance of the nature and the position with halogeno atom on the benzamide scaffold, the length chain but also the contribution of the hydrophobic part on the amine group. Among them, compounds 7i, w, y with Cl, CN or NO2 groups at the 4-position of the benzamide scaffold showed excellent affinity for S1R (Ki = 1.2–3.6 nM), selectivity for S2R (Ki up to 1400 nM) and high selectivity index (IC50(SY5Y)/Ki (S1R) ratio from 28 000 to 83 000). Futhermore, these compounds presented an excellent safety profile over 40 other receptors. These derivatives will be selected for further biological investigations.
- Donnier-Maréchal, Marion,Carato, Pascal,Larchanché, Paul-Emmanuel,Ravez, Séverine,Boulahjar, Rajaa,Barczyk, Amélie,Oxombre, Bénédicte,Vermersch, Patrick,Melnyk, Patricia
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p. 964 - 978
(2017/08/01)
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- Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines
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The first general procedure for the synthesis of 5- to 7-membered cyclic iminoethers by microwave-assisted cyclization of ω-amido alcohols promoted by polyphosphoric acid (PPA) esters is presented. 2-Aryl-2-oxazolines and 5,6-dihydro-4H-1,3-oxazines were efficiently prepared using ethyl polyphosphate/CHCl3. Trimethylsilyl polyphosphate in solvent-free conditions allowed for the synthesis of hitherto-unreported 4,5,6,7-tetrahydro-1,3-oxazepines. The method involves good to excellent yields and short reaction times.The reaction mechanism and the role of PPA esters were investigated in a chiral substrate.
- Mollo, María C.,Orelli, Liliana R.
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supporting information
p. 6116 - 6119
(2016/12/09)
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- S-Co(II) cascade catalysis: Cyclocondensation of aromatic nitriles with alkamine
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A solvent-free S/Co(NO3)2 cascade catalyzed cyclocondensation reaction of aromatic nitriles with 3-amino-1-propanol or 2-aminoethanol has been successfully developed under thermal and microwave conditions. By this two-component protocol, mono- and bis-oxazines and oxazolines were selectively synthesized both in good to excellent yields and short reaction times. This catalytic system exhibits excellent chemoselectivity, and can be reused at least seven times without significant loss of activity in subsequent reactions.
- Ge, Haixia,Liu, Ping,Li, Xiangnan,Sun, Wei,Li, Jianli,Yang, Bingqin,Shi, Zhen
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p. 6591 - 6597
(2013/07/26)
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- A green and selective synthesis of 2-aryloxazines and 2- aryltetrahydropyrimidines
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An efficient method for the selective synthesis of 2-substituted oxazines and tetrahydropyrimidines by the reaction of arylnitriles with 3-amino-1-propanol and 1,3-diaminopropane in the presence of montmorillonite K-10 and KSF as inexpensive, environmenta
- Mohammadpoor-Baltork, Iraj,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Eskandari, Zohre
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experimental part
p. 479 - 483
(2011/05/14)
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- Ultrasound promoted selective synthesis of 2-aryl-5,6-dihydro-4H-1,3-oxazines catalyzed by K-10 and KSF montmorillonite clays: A practical procedure under mild and solvent-free conditions
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Montmorillonite K-10 and KSF were found to be highly efficient, environmentally friendly and recyclable heterogeneous catalysts for the selective synthesis of a variety of 2-aryl-5,6-dihydro-4H-1,3-oxazines from arylnitriles and 3-amino-1-propanol under ultrasound irradiation. This new methodology provides excellent yields in short reaction times (10-25 min). The reaction work-up is very simple and the catalysts can be easily separated from the reaction mixture and reused several times in subsequent reactions. This catalytic system also exhibits excellent chemoselectivity in the synthesis of mono-oxazines from dinitriles.
- Mohammadpoor-Baltork, Iraj,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Eskandari, Zohre
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experimental part
p. 857 - 862
(2011/10/09)
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- H3PW12O40: An efficient and recyclable heterogeneous catalyst for the selective synthesis of 2-Aryl-5,6-dihydro-4H-1,3- oxazines and 2-Aryl-1,4,5,6-tetrahydropyrimidines
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An environmentally friendly and highly efficient procedure has been developed for the selective synthesis of 2-aryl-5,6-dihydro-4H-1,3-oxazines and 2-aryl-1,4,5,6-tetrahydropyrimidines by cyclocondensation of arylnitriles with 3-amino-1-propanol and 1,3-diaminopropane in the presence of catalytic amounts of H3PW12O40 under thermal conditions and MW irradiation. Under the same reaction conditions, dicyanobenzenes are transformed to their corresponding mono-oxazines and monotetrahydropyrimidines with excellent chemoselectivity. These reactions are simple and clean, giving the products in high yields and high purity. The catalyst can be easily recovered after the reaction and reused efficiently in subsequent runs.
- Mohammadpoor-Baltork, Iraj,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Eskandari, Zohre
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experimental part
p. 461 - 469
(2010/10/01)
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- Facile Syntheses of Oxazolines and Thiazolines with N-Acylbenzotriazoles under Microwave Irradiation
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Microwave reactions of 2-amino-2-methyl-1-propanol (2) or 2-aminoethanethiol hydrochloride (4) with readily available N-acylbenzotriazoles 1a-j in the presence of SOCl2 produced 2-substituted 2-oxazolines 3a-j in 84-98% yields and 2-substituted
- Katritzky, Alan R.,Cai, Chunming,Suzuki, Kazuyuki,Singh, Sandeep K.
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p. 811 - 814
(2007/10/03)
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- TRANSFORMATIONS OF PYRIDINIUMS DERIVED FROM AMINO-ALCOHOLS AND FROM DIAMINES
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Pyridiniums derived from amino alcohols cyclise to ethers or rearrange to aldehydes on heating.Monopyridiniums from diamines can be acylated or converted into ureas or thioureas: these products cyclise on heating in solution to give dihydro-thiazoles, -4H-thiazines, -oxazoles, -4H-oxazines, or tetrahydro-3H-thiazepines.
- Katritzky, Alan R.,Langthorne, Roland T.,Patel, Ranjan C.,Lhommet, Gerard
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p. 2383 - 2390
(2007/10/02)
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