- Synthesis of Novel Pterocarpen Analogues via [3?+?2] Coupling-Elimination Cascade of α,α-Dicyanoolefins with Quinone Monoimines
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By employing triethylamine as a catalyst, [3?+?2] coupling-elimination cascade of α,α-dicyanoolefins with quinone monoimines was realized. The reactions afforded various novel pterocarpen analogues with generally moderate yields (up to 75%). In addition, a plausible reaction mechanism was proposed.
- Chen, Hui,Zhao, Sihan,Cheng, Shaobing,Dai, Xingjie,Xu, Xiaoying,Yuan, Weicheng,Zhang, Xiaomei
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p. 1672 - 1683
(2019/04/08)
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- An Electrophilic Trifluoromethylthiolation of Silylenol Ethers and β-Naphthols with Diethylaminosulfur Trifluoride and (Trifluoromethyl)trimethylsilane
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An efficient and general trifluoromethylthiolation of silylenol ethers and β-naphthols have been accomplished employing the combination of diethylaminosulfur trifluoride (DAST) and (trifluoromethyl)trimethylsilane (CF3TMS) as source of electrophilic trifluoromethylthio moiety for the synthesis of α-trifluoromethylthiolated carbonyl compounds and β-naphthols in good yields. Important features of this method include wide functional group tolerance and use of readily available DAST/CF3TMS. Potential of the methodology was demonstrated via the synthesis of α-trifluoromethylthiolated (+)-4-cholesten-3-one and naphthoquinone. (Figure presented.).
- Saravanan, Perumal,Anbarasan, Pazhamalai
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supporting information
p. 2894 - 2899
(2018/08/17)
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- Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid
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Enantioselective [3+2] coupling of cyclic enamides with quinone monoimines was realised using a chiral phosphoric acid as a catalyst. This transformation allowed for the synthesis of highly enantioenriched polycyclic 2,3-dihydrobenzofurans (up to 99.9% ee). The absolute configuration of one product was determined by an X-ray crystal structural analysis. We also found a possible mechanism for this reaction.
- Zhang, Minmin,Yu, Shuowen,Hu, Fangzhi,Liao, Yijun,Liao, Lihua,Xu, Xiaoying,Yuan, Weicheng,Zhang, Xiaomei
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supporting information
p. 8757 - 8760
(2016/07/15)
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- 4,5-DIHYDRONAPHTHO [1,2-b] THIOPHENE DERIVATIVE
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A 4,5-dihydronaphtho[1,2-b]thiophene derivative expressed by the formula: (wherein R1 is a C1 to C10 1-hydroxyalkyl group or a C1 to C10 acyl group, and R2 and R3 separately substitute in the 6-, 7-, 8-, or 9-positions, and are each independently a hydrogen atom, a halogen atom, a C1 to C10 alkyl group, a hydroxy group, a C1 to C10 alkoxy group, a C1 to C5 alkenyloxy group, a C1 to C5 alkynyloxy group, a benzyloxy group, or the like, provided that when R1 is an acyl group and R2 is a hydrogen atom, then R3 is neither a hydrogen atom nor an acetyl group), or a pharmaceutically acceptable salt thereof. This is a novel compound that is effective in reducing triglyceride levels in the liver and reducing blood glucose levels.
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Page/Page column 10
(2010/11/08)
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- AMINO ALCOHOL COMPOUND
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A pharmaceutical composition is provided that has a low toxicity, demonstrates superior physicochemical properties and pharmacokinetics, and has superior peripheral blood lymphocyte count lowering activity. The pharmaceutical composition contains a compound having general formula (I): (wherein R 1 represents a methyl group or an ethyl group, R 2 represents a methyl group or an ethyl group, and R 3 represents a phenyl group substituted with 1 to 3 substituents selected from the group consisting of a halogen atom, a lower alkyl group, a cycloalkyl group, a lower alkoxy group, a halogeno lower alkyl group, a lower aliphatic acyl group and a cyano group), a pharmacologically acceptable salt thereof or a pharmacologically acceptable ester thereof.
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Page/Page column 54-55
(2010/11/25)
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- Synthesis of (±)-7,8- and 5,6-dimethyl-2-(2-hydroxyisopropyl) tetralins
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7,8-Dimethyl-l-tetralone 4 on sodium borohydride reduction followed by Vilsmeier-Haack reaction furnishes 7, 8-dimethyl-3,4-dihydro-2-naphthaldehyde 10. Reduction of 10 followed by oxidation with Jones reagent yields 7, 8-dimethyl-1,2,3,4-tetrahydro-2-naphthoic acid 12 which on treatment with excess of methyllithium affords 7, 8-dimethyl-2-(2-hydroxyisopropyl) tetralin 2. 5,6-dimethyl-l-tetralone 5 is converted into the 5,6-dimethyl-2-(2-hydroxyisopropyl)tetralin 3 by following similar set of reactions as described above.
- Kadam,Desai,Mane
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p. 752 - 756
(2007/10/03)
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- Synthesis of 1,1,5,6-tetramethyl-and 7-isopropyl-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene
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4-(2,3-Dimethylphenyl)butanoic acid (4) was treated with excess of methyllithium to yield 5-(2,3-dimethylphenyl)-2-methylpentan-2-ol (6) which was cyclodehydrated using Dowex 50W-X8 resin, trifluoroacetic acid or polyphosphoric acid (PPA) to furnish 1,1,5,6-tetramethyl-1,2,3,4-tetrahydronaphthalene (1). The acid 4 was cyclized with PPA to furnish 5,6-dimethyl-3,4-dihydronaphthalen-1(2H)-one (5) which was converted into 1 by reaction with dimethylzinc and titanium tetrachloride. 4-(4-Isopropylphenyl)butanoic acid (7) on esterification followed by Grignard reaction with methylmagnesium iodide furnished 5-(4-isopropylphenyl)-2-methylpentan-2-ol (9), which was cyclodehydrated as above to yield 7-isopropyl-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (2).
- Mane, Ramchandra Bhimrao,Kadam, Abhijit Jaysingrao,Salunkhe, Rajashree Sandeep
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p. 527 - 532
(2007/10/03)
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- Phosphonic acid compounds, their production and use
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The present invention relates to a compound of the general formula (I): STR1 wherein ring A is a benzene ring that may be substituted; Y is a divalent group as a constituent member of ring B forming a 5- to 8-membered ring; Q1 is a group of the formula --X--P(O)(OR1)(OR2) wherein X is a bond or a divalent group; R1 and R2, identical or different, are hydrogen or a lower alkyl, or may be combined together to form a ring; Q2 is hydrogen, a hydrocarbon group that may be substituted or a heterocyclic group that may be substituted; and the group of the formula --CON(Q1)(Q2) is connected to the a- or b-position carbon atom, or a salt thereof, which is useful as prophylactic and therapeutic agents of various metabolic bone diseases such as osteoporosis.
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- Synthesis of substituted chrysenes and phenanthrenes
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3-Methylchrysene (9a), 2, 3, 9-trimethylchrysene (9b), 2, 6-dimethylphenanthrene (16a) and 1-isopropyl-4,6-dimethylphenanthrene (16b) have been synthesised in the following steps. β-(1-Naphthyl)ethyl bromide (6a), β-(6,7-dimethyl-1-naphthyl)ethyl bromide (6b), β-(3-methylphenyl)ethyl bromide (13a) and β-(2-isopropyl-5-methylphenyl)ethyl bromide (13b) are separately condensed with potassium salt of 1-carbethoxy-4-methylcyclohexane-2-one (1) to give respectively 7a, 7b, 14a and 14b. PPA cyclisation of 7a and 7b affords 8a and 8b while 14a affords 15a and 14b gives a mixture of 15b and 15c. Aromatisation of 8a and 8b leads to 9a and 9b and that of 15a gives 16a while 15b and 15c both produce 16b. The structures assigned are consistent with their spectral data.
- Mitra, Ashutosh,Ghoshe, Swati
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p. 785 - 789
(2007/10/03)
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- SCHWEFELVERBINDUNGEN DES ERDOELS XV. METHYL-5,6,7,8-TETRAHYDRODINAPHTHOTHIOPHENE UND METHYLDINAPHTHOTHIOPHENE
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A one pot synthesis gives methyl-5,6,7,8-tetrahydrodinaphthothiophenes (7) from methyl-1,2,3,4-tetrahydronaphthalen-1-ones (1) by bromination and sulfurization.Tetrahydro compounds 7 have been dehydrogenated to corresponding dinaphthothiophenes 8.Proofs for the constitutions are nmr data of 7, 8 and the independent synthesis of one compound 8.A reaction mechanism with 1,4-dithiine intermediates is discussed. Key words: Alkyl-1,2,3,4-tetrahydronaphthalen-1-ones; alkyl-5,6,7,8-tetrahydrodinaphthothiophenes; alkyldinaphthothiophenes; dehydrogenation with o-chlorobenzoquinone.
- Boberg, Friedrich,Jachiewicz, Adam,Garming, Alfons
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