- Diastereoselective synthesis of 2,4-disubstituted tetrahydropyranols and ethers via a prins-type cyclization catalyzed by scandium triflate
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The reaction of aldehydes with homoallylic alcohols catalyzed by scandium triflate gives rise to the formation of 2-substituted tetrahydropyran-4-ols and ethers in good overall yields and with 'all-cis' configurations and high diastereoselectivities. The
- Zhang, Wen-Chun,Li, Chao-Jun
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- Direct formation of tetrahydropyranols via catalysis in ionic liquid
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Utilizing a simple homoallyl alcohol and an aldehyde in the presence of a catalytic amount of cerium triflate, the direct stereoselective formation of tetrahydropyranol derivatives in ionic liquid is reported.
- Keh, Charlene C.K,Namboodiri, Vasudevan V,Varma, Rajender S,Li, Chao-Jun
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- Scandium triflate catalyzed in situ Prins-type cyclization: Formations of 4-tetrahydropyranols and ethers
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The reaction of aldehydes with homoallyl alcohols catalyzed by scandium triflate generates tetrahydropyran-4-ol and ethers in good yields.
- Zhang, Wen-Chun,Viswanathan, Ganapathy S.,Li, Chao-Jun
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- Identification of a novel and orally available benzimidazole derivative as an NPY Y5 receptor antagonist with in vivo efficacy
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Optimization of lead compound 2 is described, mainly focusing on modification at the C-2 position of the benzimidazole core. Replacement of the phenyl linker of 2 with saturated rings resulted in identification of compound 8b which combines high Y5 recept
- Tamura, Yuusuke,Omori, Naoki,Kouyama, Naoki,Nishiura, Yuji,Hayashi, Kyouhei,Watanabe, Kana,Yukioka, Hideo,Sato, Hiroki,Okuno, Takayuki,Tanaka, Yukari,Chiba, Takeshi
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p. 6554 - 6558,5
(2012/12/12)
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- Investigation of Prins reaction for the synthesis of 2, 4-disubstituted tetrahydropyran derivatives and 1, 3-dioxanes using polyaniline supported acid as reusable catalyst
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The Prins cyclization of homoallyl alcohol with a variety of aldehydes were observed under reflux condition in dichloromethane using both polyaniline supported TsOH (PANI-TsOH) and FeCl3 (PANI- FeCl3) as reusable acid catalysts with the formation of 2,4-disubstituted tetrahydropyran ether as single product. In case of 4-, 3- and 2- nitro benzaldehydes, the reaction generated acetal of the aldehyde and homoallylic alcohol as single product. Additionally, both catalysts were investigated for the synthesis of 1, 3-dioxane in dichloromethane under reflux and at ambient temperature Indian Academy of Sciences.
- Borah, Kalyan Jyoti,Borah, Ruli
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experimental part
p. 623 - 630
(2012/07/14)
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- NOVEL PIPERIDINYL-1,3-DIHYDRO-BENZOIMIDAZOL-2-ONES AS M1 AGONISTS
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The present invention relates to novel M1 agonistic compounds of the present invention and their use in the treatment of cognitive impairment associated i.a. with schizophrenia and in the treatment of other diseases mediated by the muscarinic M1 receptor.
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Page/Page column 36
(2009/11/29)
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- The 'aqueous' Prins cyclization: A diastereoselective synthesis of 4-hydroxytetrahydropyran derivatives
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Phosphomolybdic acid (H3PMo12O40, a heteropoly acid) is found to catalyze efficiently the Prins cyclization of homoallylic alcohols with aldehydes in water at room temperature to provide tetrahydropyran-4-ol derivatives in high yields with all cis-selectivity. Only cyclic ketones can give spirocyclic products. The use of phosphomolybdic acid in water makes this procedure simple, more convenient, cost-effective, and environmentally friendly. Georg Thieme Verlag Stuttgart.
- Yadav, Jhillu S.,Subba Reddy, Basi V.,Narayana Kumar, Gunda G. K. S.,Aravind, Seema
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p. 395 - 400
(2008/09/20)
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- Bismuth triflate catalyzed prins-type cyclization in ionic liquid: Synthesis of 4-tetrahydropyranol derivatives
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The reaction of aldehydes with homoallylic alcohols in the presence of catalytic amount of bismuth triflate in [bmim]PF6generates 4-tetrahydropyranol derivatives in excellent yield and with high diastereoselectivity.
- Murty,Rajasekhar,Harikrishna,Yadav
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p. 104 - 106
(2008/04/05)
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- New Oxetane and Tetrahydropyran Synthesis
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The base catalysed rearrangement of the benzyl ethers of oxiranylcarbinols and their homologues provides convenient routes to oxetan-3-ylcarbinols and tetrahydropyran-4-ols.
- Bird, C.W.,Hormozi, N.
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p. 1777 - 1780
(2007/10/02)
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- Enzymes in Organic Synthesis. 25. Heterocyclic Ketones as Substrates of Horse Liver Alcohol Dehydrogenase. Highly Stereoselective Reductions of 2-Substituted Tetrahydropyran-4-ones
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Horse liver alcohol dehydrogenase (HLADH) has been found to be an efficient catalyst for the reduction of O-heterocyclic ketones.Preparative-scale HLADH-catalyzed reductions of 2-substituted tetrahydropyran-4-ones are enantioselective, with reduction of e
- Haslegrave, J. Anthony,Jones, J. Bryan
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p. 4666 - 4671
(2007/10/02)
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