- Cascade formation of isoxazoles: Facile base-mediated rearrangement of substituted oxetanes
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Give me five! Nitro compounds and oxetan-3-one react through an intriguing cascade sequence to give isoxazole-4-carbaldehydes using inexpensive reagents in a one-pot procedure (see scheme; Ms=methanesulfonyl). A variety of 3-substituted isoxazole-4-carbaldehydes were obtained in high overall yields.
- Burkhard, Johannes A.,Tchitchanov, Boris H.,Carreira, Erick M.
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supporting information; scheme or table
p. 5379 - 5382
(2011/07/08)
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- Acyl iodides in organic synthesis: II. Reactions with acyclic and cyclic ethers
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Reaction of acyl iodides RCOI (R = Me, Ph) was studied with acyclic and cyclic ethers (Et2O, MeCHCH2(O), ClCH2CHCH 2(O), THF, O(CH2CH2)2O, EtOCH 2CH2OH, EtOCH=CH2, PhOEt]. The reaction occurred with the rupture of one or two CO bonds furnishing the corresponding iodides and esters.
- Voronkov,Trukhina,Vlasova
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p. 1579 - 1581
(2007/10/03)
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- Highly regioselective cleavages and iodinations of cyclic ethers utilizing SmI2
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Various functionalized cyclic ethers such as oxiranes, oxetanes, and tetrahydrofurans have been prepared, and the regiochemistry of their ring opening with samarium diiodide and acyl chloride or anhydride has been investigated. Alkyl-substituted oxetane 5 and tetrahydrofurans 1 and 2 show almost no regioselectivity. However, high regioselectivities from the branched cyclic ethers (3, 8, 9, and 10) containing ethereal or hydroxyl moieties have been observed. This is probably the result of the bidentate chelated species between samarium and oxygen.
- Kwon, Doo Won,Kim, Yong Hae,Lee, Kieseung
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p. 9488 - 9491
(2007/10/03)
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- Scavenger assisted combinatorial process for preparing libraries of tertiary amine compounds
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This invention relates to a novel solution phase process for the preparation of tertiary amine combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.
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- A remarkably simple process for monoprotecting diols
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Lipase from pig pancreas (PPL) has been shown to catalyse selectively the hydrolysis of alkane-1,n-diol bis-acetates into the corresponding monoacetate.
- Houille, Olivier,Schmittberger, Thierry,Uguen, Daniel
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p. 625 - 628
(2007/10/02)
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- A versatile approach to cyclic ethers. Synthesis of disubstituted oxepanes and oxocanes
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A synthetic sequence for the preparation of α,α'-disubstituted cyclic ethers of various ring sizes and either relative stereochemistry (cis or trans) is presented. It is based on the hetero Diels Alder reaction of a monoactivated diene and an aldehyde, yi
- Teresa Mujica,Afonso, Maria M.,Galindo, Antonio,Antonio Palenzuela
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p. 3401 - 3404
(2007/10/02)
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- Synthesis of novel pyridazine acyclonucleosides
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Some pyridazine acyclonucleosides containing hydroxymethyl and 4-hydroxybutyl groups as an alkanol side chain were prepared. Nucleophilic displacement of N1-alkyl-4,5-dichloropyridazin-6-ones is discussed.
- Cho,Chung,Choi,Kim,Yoon
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p. 1199 - 1208
(2007/10/02)
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- Synthesis of long chain ω-aralkylbromides
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1-Iodo-4-acetoxybutane is a useful 4 carbon synthon which reacts selectively with Grignards under copper catalysis. The immediate products are converted to bromides.
- Forth,Smith
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p. 951 - 959
(2007/10/02)
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- LITHIUM TELLUROCARBOXYLATES: SYNTHESIS AND CHARACTERIZATION
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A series of lithium tellurocarboxylates (1) were obtained as orange to red oils containing an equivalent of lithium telluride.The salts (1) are extremely sensitive towards oxygen.Lithium benzenecarbotelluroate (1d) reacted with isopropyl iodide to give Te
- Kato, Shinzi,Sasaki, Hirotomo,Yagihara, Morio
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- Asymmetric Synthesis of Benzoin by SmI2-Mediated Enantioselective Protonation
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Samarium (Z)-1,2-diphenylethen-1,2-diolate, which is considered to be an intermediate of a SmI2-mediated reduction of benzil, was protonated enantioselectively by quinidine to afford (R)-benzoin in 91 percentee.It was found that quenching the unreacted en
- Takeuchi, Seiji,Miyoshi, Norikazu,Hirata, Kenji,Hayashida, Haruyoshi,Ohgo, Yoshiaki
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p. 2001 - 2003
(2007/10/02)
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- SELECTIVE CLEAVAGE OF ETHERS BY SODIUM IODIDE - ACYL CHLORIDE
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Cyclic and acyclic ethers are regioselectively cleavaged at less substituted α-carbon-oxygen bond in the absence of Lewis acid by the reagent system of sodium iodide and acyl chlorides.
- Oku, Akira,Harada, Toshiro,Kita, Kazuhiro
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p. 681 - 684
(2007/10/02)
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- Anesthesia methods using benzopyrans and esters thereof as pre-anesthesia medication
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Improved anesthesia methods comprising pretreating a patient to be anesthetized with a benzopyran of formula I STR1 wherein, in the C ring, X is NR1, S, CH2 or STR2 R1 is hydrogen, loweralkyl, loweralkenyl, loweralkynyl, loweralkanoyl, cycloalkyloweralkyl, cycloalkylloweralkanoyl, cycloalkyl, haloloweralkyl, haloloweralkenyl, phenylloweralkyl, phenyloweralkenyl or phenyloweralkylnyl; m is an integer from 0 to 3, n is an integer from 0 to 3 and n + m = 2 or 3; or the C ring is quinuclidine ring STR3 R2 is loweralkyl; R3 is hydrogen or STR4 wherein Y is a straight or branched chain alkylene group having from one to eight carbon atoms, a is an integer from 1 to 4, b is an integer from 1 to 4, Z is CH2, O, S or NR6, R6 being hydrogen or loweralkyl, with the limitation that when Z is O, S or NR5, the sum of a and b is 3 or 4, and R5 is hydrogen or loweralkyl; R4 is C1 -C20 straight or branched chain alkyl, cycloalkyl, or STR5 wherein Y is a straight or branched chain alkylene group having from one to ten carbon atoms, and each R7, R8 and R9 are the same or different members of the group consisting of hydrogen, halo, trifluoromethyl or loweralkyl; and the pharmaceutically acceptable salts thereof, with the limitation that when X is STR6 m = 2 and n = 2, R3 cannot be hydrogen.
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