- Application of "click" chemistry in solid phase synthesis of alkyl halides
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A convenient and highly selective microwave assisted procedure for the conversion of allylic, benzylic and aliphatic alcohols to their corresponding halides using polymer-bound triphenylphosphine and iodine is presented. In case of symmetrical diols, mono-iodination product is obtained in very high yield. Additionally, highly regioselective behavior is observed in our procedure. Simplicity in operation, no column chromatography required for the purification of the products, recyclability of the reagents used, short reaction times and good to excellent yields are the advantages of our protocol. Most functional groups remain unaffected under our reaction condition.
- Das, Diparjun,Chanda, Tridib,Rokhum, Lalthazuala
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p. 775 - 783
(2016/01/20)
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- Rh(II)-catalyzed enantioselective synthesis of acuminatin through a C-H insertion reaction of a non-stabilized carbenoid
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An efficient and practical asymmetric synthesis of the 2,3-dihydrobenzo[b] furan neolignan acuminatin was achieved by using trans-isoeugenol as the starting material. The key step is an intramolecular C-H insertion through a non-stabilized carbenoid, prep
- López-Sánchez, Cristóbal,álvarez-Corral, Míriam,Jiménez-González, Leticia,Mu?oz-Dorado, Manuel,Rodríguez-García, Ignacio
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p. 5511 - 5516
(2013/07/05)
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- Efficient and selective iodination of benzylic alcohols using NaI/bronsted ionic liquid system at room temperature
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A simple, chemoselective, and effective procedure for the conversion of benzylic and allylic alcohols into corresponding iodides using NaI in the presence of a catalytic amount of 3-methylimidazolium hydrogensulfate ([Hmim]+[image omitted]) at room temperature is reported.
- Hajipour, Abdol R.,Rafiee, Fatemeh,Ruoho, Arnold
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experimental part
p. 603 - 611
(2011/04/15)
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- Iodination of alcohols under microwave irradiation using KI in the presence of a catalytic amount of ionic liquid triethylamoniom hydrogensulfate([Et 3NH]+HSO4-)
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The iodination of alcohols with KI in the presence of a catalytic amount of triethylamoniom hydrogensulfate ([Et3NH]+HSO 4-) as a novel and inexpensive ionic liquid under microwave irradiation has been investigated. Copyright Taylor & Francis Group, LLC.
- Hajipour, Abdol R.,Azizi, Ghobad,Ruoho, Arnold E.
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experimental part
p. 242 - 250
(2009/04/07)
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- Efficient method for iodination of alcohols using KI/silica sulfuric acid (SSA)
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A straightforward and effective procedure for the conversion of benzylic and allylic alcohols to the corresponding iodides using KI/SSA in acetonitrile at room temperature. Copyright Taylor & Francis Group, LLC.
- Hajipour, Abdol R.,Zarei, Amin,Ruoho, Aronold E.
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p. 1039 - 1050
(2007/10/03)
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- Iodination of alcohols using triphenylphosphine/iodine under solvent-free conditions using microwave irradiation
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A straightforward and effective procedure for the conversion of benzylic, allylic and aliphatic alcohols to the corresponding iodides using Ph3P/I2 under solvent-free conditions using microwave irradiation is reported.
- Hajipour, Abdol Reza,Falahati, Ali Reza,Ruoho, Arnold E.
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p. 4191 - 4196
(2007/10/03)
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- An alternative method for the highly selective iodination of alcohols using a CsI/BF3·Et2O system
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A variety of allylic and benzylic alcohols have been converted into the corresponding iodides using cesium iodide (CsI) in the presence of boron trifluoride etherate (BF3·Et2O) in acetonitrile under mild conditions.
- Hayat, Safdar,Atta-Ur-Rahman,Khan, Khalid Mohammed,Choudhary, M. Iqbal,Maharvi, Ghulam Murtaza,Zia-Ullah,Bayer, Ernst
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p. 2531 - 2540
(2007/10/03)
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- 5-amino-4-hydroxyhexanoic acid derivatives
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Compounds of formula I STR1 or their hydroxy-protected derivatives, and compounds of formula I' STR2 wherein T is an acyl radical of formula Z STR3 wherein Rz is unsubstituted or substituted hydrocarbyl wherein at least one carbon atom has been replaced by a hetero atom with the proviso that a hetero atom is not bonded directly to the carbonyl to which the radical Rz is bonded, alkyl having two or more carbon atoms, lower alkenyl, lower alkynyl, aryl or unsubstituted or substituted amino, and wherein the radicals R1, B1, R2, R3, A1, A2 and NR4 R5 are as defined in the description, and precursors thereof, are described. The compounds have pharmaceutical activity, for example in the treatment of retroviral diseases, such as AIDS.
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- ANTIVIRAL ETHERS OF ASPARTATE PROTEASE SUBSTRATE ISOSTERES
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Antiretroviral compounds (which are effective, for example, against HIV) of the formula I STR1 in which R 1 is an acyl radical lower-alkoxyl-lower-alkanoyl whose lower alkoxy radical is unsubstituted or is substituted by halogen, phenyl, lower alkoxy or a heterocyclic radical selected from piperidinyl, pyrrolidinyl, tetrahydropyranyl, tetrahydrofuranyl, thiazolidinyl, thiazolyl, indolyl or 4H-1-benzopyranyl which is unsubstituted or substituted by oxo, hydroxyl, amine, lower alkyl, lower-alkoxycarbonyl and/or phenyl-lower-alkoxycarbonyl; lower alkanoyl which is unsubstituted or is substituted by one of the said unsubstituted or substituted heterocyclic radicals; arylcarbonyl or heterocyclylcarbonyl which are substituted by heterocyclyl or heterocyclyl-lower-alkyl; phenyl-lower-alkanoyl which is substituted by hydroxyl and lower alkyl; or arylsulfonyl;or the residue of an amino acid which is defined in accordance with the description (and which may be acylated on the amino nitrogen by one of the abovementioned acyl radicals);R 2 and R 3 are in each case cyclohexyl, cyclohexenyl, phenyl, naphthyl or tetrahydronaphthyl which are unsubstituted or substituted by lower alkyl, phenyl, cyanophenyl, phenyl-lower-alkyl, halogen, halo-lower-alkyl, cyano, hydroxyl, lower alkoxy, phenyl-lower-alkoxyl, pyridyl-lower-alkoxy, lower-alkoxy-lower-alkoxy, lower-alkoxycarbonyl-lower-alkoxy, carboxyl-lower-alkoxy, hydroxyl-lower-alkoxy, carbamoyl-lower-alkoxy, cyano-lower-alkoxy, and phenyl-lower-alkanesulfonyl which is unsubstituted or substituted by halogen;R 4 is lower alkyl, cyclohexyl or phenyl; and R 5 is lower alkyl; and n is 1 or 2, or salts thereof, are novel.
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- Preparation of α-Branched Phenylalanines and of 1,1-Disubstituted Ethylenediamines via Chiral Imidazolidinones and Oxazolidinones of Glycine - Preparative and Mechanistic Aspects
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To test the structural prerequisites for a new carbanionoid rearrangement of 3-methyl-2-pivaloyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid to N-(t-butoxycarbonyl)-1-amino-2-methylindan-2-carboxylic acid (A -> B), various α-branched phenylalanines (
- Seebach, Dieter,Gees, Thomas,Schuler, Franz
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p. 785 - 800
(2007/10/02)
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- Diiodosilane. 2. A Multipurpose Reagent for Hydrolysis and Reductive Iodination of Ketals, Acetals, Ketones, and Aldehydes
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The reaction patterns of diiodosilane (SiH2I2, DIS) with ketals, acetals, ketones, and aldehydes were explored.The reagent may be used for mild cleavage of ketals and acetals either hydrolytically to give the parent carbonyl functionality or reductively to produce the corresponding alkyl iodide.At low temperatures (-42 deg C) and short reaction times (few minutes), catalytic amounts (5-10 molpercent) of DIS provide clean deprotection of various ketals and acetals to yield ketones and aldehydes, with no apparent reduction of the latter.At temperatures above 0 deg C, DIS effectively reduces ketals and acetals to iodoalkanes.This reduction is quite general both with respect to ketals and acetals and unprotected ketones and aldehydes.Reaction rates, however, are strikingly dependent on the substrate, with the following tendencies: (a) aromatic functionalities are generally reduced much faster than their aliphatic analogues; (b) ketals and acetals are rapidly reduced to the corresponding iodoalkanes, while free aldehydes, and particularly ketones, are essentially inert under the reaction conditions (but can be significantly activated by catalytic amounts of iodine); (c) dimethyl ketals form the parent ketones preferentially, while all other ketals, including diethyl ketals and dioxolanes, are reduced to iodoalkanes.
- Keinan, E.,Perez, D.,Sahai, M.,Shvily, R.
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p. 2927 - 2938
(2007/10/02)
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