cas 19740-72-8, diisopropyl bicarbamate | Articles data

Articles about 19740-72-8Total 29 be found

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The effect of acid strength on the Mitsunobu esterification reaction: Carboxyl vs hydroxyl reactivity
In the presence of carboxylic acids, the adduct formed between triphenylphosphine and diisopropyl azodicarboxylate reacts to form mono- and bis-acylated hydrazides and the carboxylic acid anhydrides. These products are formed via attack of the carboxylate on the triphenylphosphonium group of the adduct, with weaker acids reacting much faster than stronger acids. This provides an explanation for the observation in the literature that acids stronger than acetic acid, such as 4-nitrobenzoic acid and chloroacetic acid, provide better yields in esterification reactions, since reaction of the alcohol with the phosphonium group of the adduct is more rapid than the competing reaction of the carboxylate for the phosphonium group.
Hughes, David L.,Reamer, Robert A.
p. 2967 - 2971
(1996)
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The formation of anhydrides in the Mitsunobu reaction
Treatment of benzoic acid with triphenylphosphine and diisopropyl azodicarboxylate in THF or acetonitrile, results in the formation of benzoic anhydride. A significant solvent effect was observed for this reaction. Anhydride formation did not occur however with the more acidic p-nitrobenzoic acid. Relative rate and competition experiments suggest that the improved yields observed when p-nitrobenzoic acid is used instead of benzoic acid in the Mitsunobu esterification reaction are due to competitive anhydride formation in the latter case.
Harvey, Peta J.,Von Itzstein, Mark,Jenkins, Ian D.
p. 3933 - 3942
(1997)
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1,2-DIALKOXYCARBONYLHYDRAZINE DERIVATIVES OF PYRROLES AND INDOLIZINES. A NEW SYNTHESIS OF CYCLAZINES
The reaction of pyrroles 1 with diisopropyl azodicarboxylate 2 yields 2- and 2,5-substituted derivatives. 3- and 1,3-substituted indolizines 5 and 6 are formed by the same route.Cyclazines 7 have been obtained from 5 and 6 with dimethyl acetylenedicarboxylate.
Flitsch, Wilhelm,Heinrich, Juergen
p. 3673 - 3676
(1980)
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Decarboxylative Amination: Diazirines as Single and Double Electrophilic Nitrogen Transfer Reagents
The ubiquity of nitrogen-containing small molecules in medicine necessitates the continued search for improved methods for C-N bond formation. Electrophilic amination often requires a disparate toolkit of reagents whose selection depends on the specific structure and functionality of the substrate to be aminated. Further, many of these reagents are challenging to handle, engage in undesired side reactions, and function only within a narrow scope. Here we report the use of diazirines as practical reagents for the decarboxylative amination of simple and complex redox-active esters. The diaziridines thus produced are readily diversifiable to amines, hydrazines, and nitrogen-containing heterocycles in one step. The reaction has also been applied in fluorous phase synthesis with a perfluorinated diazirine.
Chandrachud, Preeti P.,Wojtas, Lukasz,Lopchuk, Justin M.
supporting information
p. 21743 - 21750
(2021/01/11)

Photocatalytic esterification under Mitsunobu reaction conditions mediated by flavin and visible light
The usefulness of flavin-based aerial photooxidation in esterification under Mitsunobu reaction conditions was demonstrated, providing aerial dialkyl azodicarboxylate recycling/generation from the corresponding dialkyl hydrazine dicarboxylate. Simultaneously, activation of triphenylphosphine (Ph3P) by photoinduced electron transfer from flavin allows azo-reagent-free esterification. An optimized system with 3-methylriboflavin tetraacetate (10%), oxygen (terminal oxidant), visible light (450 nm), Ph3P, and dialkyl hydrazine dicarboxylate (10%) has been shown to provide efficient and stereoselective coupling of various alcohols and acids to esters with retention of configuration.
M?rz,Chudoba,Kohout,Cibulka
supporting information
p. 1970 - 1975
(2017/03/11)

Copper-catalyzed C-N bond formation using dialkyl azodicarboxylate as the amination reagent
An efficient copper-catalyzed reaction for C-N bond formation using aryl halides, dialkyl azodicarboxylate, and a hydride source is reported. Using this procedure, aryl iodides reacted at ambient conditions, while aryl bromides required heating to 60 °C to accomplish the transformation. Various functional groups were tolerated under the optimum conditions.
Samzadeh-Kermani, Alireza
p. 463 - 465
(2016/01/12)

REDUCTION METHOD USING WATER AS PROTON SOURCE BY MEANS OF N-HETEROCYCLIC CARBENE
PROBLEM TO BE SOLVED: To provide a reduction method using water as a proton source by means of N-heterocyclic carbene, in which the N-heterocyclic carbene is used actively as a reaction accelerator to realize a hydrogenation reaction by using water as the proton source. SOLUTION: A solution, which is obtained by mixing: a reaction substrate shown at an upper stage of the following formulae; a precursor of the triazole-based N-heterocyclic carbene (NHC) shown at a lower stage; water; and 1,2-dimethoxyethane being a solvent, is reacted at 100°C or higher temperature for 2 hours or more while making the solution to pass through a microwave reaction unit and the reacted solution is subjected to reduced-pressure distillation to obtain a hydrogenated product. The formulae: (EWG1-EWG4 are each an ester group, a cyano group, a ketone group, an amido group or an imido group;R1-R5 are each a 1-20C aliphatic group, a 3-12C alicyclic group or 6-30C aromatic group) SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT
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Paragraph 0014; 0015; 0028

(2016/10/10)

Method of manufacturing Azodicarboxylic acid diester compd. (by machine translation)
PROBLEM TO BE SOLVED: To provide a manufacturing method in which an azodicarboxylate diester compound can be efficiently obtained in a high yield and which is industrially advantageous.SOLUTION: There is provided a manufacturing method for azodicarboxylate diester compound including: a process (a) of obtaining a 1,2-hydrazine dicarboxylate diester compound through reaction between hydrazine and a halocarbonate ester; and a process (b) of obtaining an azodicarboxylate diester compound represented by general formula (2) (where A represents a hydrocarbon or a hydrocarbon which may have an ether bond) by oxidizing the 1,2-hydrazine dicarboxylate diester compound obtained in the process (a), the 1,2-hydrazine dicarboxylate diester compound being neither isolated nor refined.
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Paragraph 0029; 0031

(2017/04/28)

Transfer hydrogenation promoted by N-heterocyclic carbene and water
N-Heterocyclic carbenes (NHCs) promote the transfer hydrogenation of various activated C=C, C=N, and N=N bonds with water as the proton source. The NHCs act as reducing reagents to be converted into their oxides. A detailed reaction mechanism is proposed on the basis of deuterium-labeling experiments.
Kato, Terumasa,Matsuoka, Shin-Ichi,Suzuki, Masato
supporting information
p. 13906 - 13909
(2015/09/07)

Reduction and hydrogenation of a diazene by a (β-diketiminato)nickel hydrazide
A (β-diketiminato)nickel(II) hydrazido(1-) complex [L tBuNi-(η2-N2H3)], {1, L tBu = [HC(CtBuNC6H3{iPr}2) 2]-} has been obtained by treatment of [LtBuNiBr] with hydrazine. In a reaction of 1 with two equivalents of the azo compound diisopropyl azodicarboxylic ester (adc-OiPr) the Ni(N2H3) entity acts as both a hydrogenating and a reducing agent: diisopropyl hydrazidodicarboxylate (hdc-OiPr) is formed, and more adc-OiPr is reduced by two electrons. The resulting (adc-OiPr)2- is found as a ligand in the ultimate nickel product complex, the trinuclear nickel(II) compound [L tBuNi(μ-adc-OiPr)Ni(μ-adc-OiPr)NiLtBu] (2), in which two LtBuNi+ units are linked by a [NiII(adc- OiPr)2]2- moiety. The hypothesis that L tBuNiI species are acting as intermediates was supported by the independent finding that 2 can also be obtained by reaction of [L tBuNi(OEt2)] with adc-OiPr.
Koethe, Claudia,Metzinger, Ramona,Limberg, Christian
p. 3937 - 3942
(2013/11/06)

Metal-free, hydroacylation of CC and NN bonds via aerobic C-H activation of aldehydes, and reaction of the products thereof
In this report, a thorough evaluation of the use of aerobically initiated, metal-free hydroacylation of various CC and NN acceptor molecules with a wide range of aldehydes is presented. The aerobic-activation conditions that have been developed are in sharp contrast to previous conditions for hydroacylation, which tend to use transition metals, peroxides that require thermal or photochemical degradation, or N-heterocyclic carbenes. The mildness of the conditions enables a number of reactions involving sensitive reaction partners and, perhaps most significantly, allows for α-functionalised chiral aldehydes to undergo radical-based hydroacylation with complete retention of optical purity. We also demonstrate how the resulting hydroacylation products can be transformed into other useful intermediates, such as γ-keto- sulfonamides, sultams, sultones, cyclic N-sulfonyl imines and amides.
Chudasama, Vijay,Akhbar, Ahmed R.,Bahou, Karim A.,Fitzmaurice, Richard J.,Caddick, Stephen
supporting information
p. 7301 - 7317
(2013/10/22)

Oxidation of alcohols to carbonyl compounds with diisopropyl azodicarboxylate catalyzed by nitroxyl radicals
A nitroxyl-radical-catalyzed oxidation of alcohols using diisopropyl azodicarboxylate (DIAD) as the terminal oxidantis reported. A variety of primary and secondary alcohols including aliphatic, benzylic, and allylic alcohols are efficiently oxidized to their corresponding aldehydes and ketones without overoxidation to carboxylic acid. 1,2-Diols are oxidized to hydroxyl ketones or diketones depending on the amount of DIAD used.
Hayashi, Masaki,Shibuya, Masatoshi,Iwabuchi, Yoshiharu
scheme or table
p. 3005 - 3009
(2012/05/04)

An Ireland-claisen rearrangement/lactonisation cascade as a key step in studies towards the synthesis of (-)-euonyminol
Progress towards the asymmetric total synthesis of (-)-euonyminol is described with the focus on the installation of the -oxygenation pattern on the lower rim of the molecule. An Ireland-Claisen rearrangement/lactonisation cascade has been developed and studies towards further elaboration have uncovered an intriguing tunable diastereoselective -bromination of the resulting γ-lactone. Georg Thieme Verlag Stuttgart · New York.
Webber, Matthew J.,Weston, Matthew,Grainger, Damian M.,Lloyd, Stacy,Warren, Sarah A.,Powell, Lyn,Alanine, Alexander,Stonehouse, Jeffrey P.,Frampton, Christopher S.,White, Andrew J. P.,Spivey, Alan C.
supporting information; experimental part
p. 2693 - 2696
(2012/01/03)

Functionalisation of aldehydes via aerobic hydroacylation of azodicarboxylates 'on' water
Herein we report the functionalisation of aldehydes via hydroacylation of azodicarboxylates. A range of functionalised aldehydes are employed as the limiting reagent including chiral non-racemic aldehydes bearing α-stereocentres which are functionalised giving access to enantiomerically pure products. The resultant hydrazides can be employed as acyl donors in the synthesis of amides.
Chudasama, Vijay,Ahern, Jenna M.,Dhokia, Dipti V.,Fitzmaurice, Richard J.,Caddick, Stephen
p. 3269 - 3271
(2011/05/02)

Targeting the Hsp90 chaperone: Synthesis of novel resorcylic acid macrolactone inhibitors of Hsp90
A series of benzo-macrolactones has been prepared by chemical synthesis, and evaluated as inhibitors of heat shock protein 90 (Hsp90), an emerging attractive target for novel cancer therapeutic agents. A new synthesis of these resorcylic acid macrolactone analogues of the natural product radicicol is described in which the key steps are the acylation and ring opening of a homophthalic anhydride to give an isocoumarin, followed by a ring-closing metathesis to form the macrocycle. The methodology has been extended to a novel series of macrolactones incorporating a 1,2,3-triazole ring.
Day, James E. H.,Sharp, Swee Y.,Rowlands, Martin G.,Aherne, Wynne,Workman, Paul,Moody, Christopher J.
supporting information; experimental part
p. 2758 - 2763
(2010/07/04)

N-heterocyclic carbene catalyzed transformations of 3-halopropenals to the equivalents of β-acylvinyl anions
[Chemical equation presented] 3-Halopropenals 1 can behave as an alternative equivalent of β-acylvinyl anions (I) In the presence of N-heterocyclic carbene precursor (IPr-HCI) and DBU to afford cyclic αβ-unsaturated carbonyl derivatives, butenolides 4 and
Wu, Yihua,Yao, Weijun,Pan, Lianjie,Zhang, Yiping,Ma, Cheng
supporting information; experimental part
p. 640 - 643
(2010/05/18)

Enantioselective syntheses of α-Fmoc-Pbf-[2-13C]-L- arginine and Fmoc-[1,3-13C2]-L-proline and incorporation into the neurotensin receptor 1 ligand, NT8-13
(Chemical Equation Presented) Enantioselective syntheses of selectively labeled, orthogonally protected [2-13C]-L-arginine and [1,3- 13C2]-L-proline are described from the commercially available precursors [2-13C]bromoacetic acid and potassium [ 13C]cyanide. Interestingly the enhanced signal assigned to C-2 in the 13C NMR spectrum of α-Fmoc-Pbf-[2-13C]-L-arginine was very broad at room temperature. The two Fmoc-labeled amino acids were used to prepare [2-13C]-Arg9 and [1,3-13C2]-Pro10 labeled ligand (NT8-13) by manual Fmoc-SPSS.
Song, Chuanjun,Tapaneeyakorn, Satita,Murphy, Annabel C.,Butts, Craig,Watts, Anthony,Willis, Christine L.
experimental part
p. 8980 - 8987
(2010/03/02)

DEAD-(cat)ZnBr2 an efficient system for the oxidation of alcohols to carbonyl compounds
The combination of diethyl azodicarboxylate (DEAD) and a catalytic amount of ZnBr2 is an efficient system for the dehydrogenation of alcohols to the corresponding carbonyl compounds. The scope and limitations of this process have been studied.
Cao, Hai Thuong,Grée, René
experimental part
p. 1493 - 1494
(2009/06/18)

Regioselective bromination of activated aromatic substrates with a ZrBr4/diazene mixture
A regioselective method for the bromination of phenols, ethers and anilines using a ZrBr4/diazene mixture is described. The reaction takes place under mild reaction conditions and the bromine atom adds first at the para unsubstituted position with respect to the OH, OR or NR2 group of the activated aromatic substrate. Less reactive compounds such as toluene, phenyl acetate, benzonitrile and trifluoromethylbenzene remain intact under the same conditions.
Stropnik, Tadej,Bombek, Sergeja,Ko?evar, Marijan,Polanc, Slovenko
p. 1729 - 1733
(2008/09/18)

VIGABATRIN BIOISOTERES AND RELATED METHODS OF USE
Compounds bioisoteric to vigabatrin and related methods of use.
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Page/Page column 9; 16

(2010/11/26)

INHIBITORS OF AKT ACTIVITY
Invented are novel 1 H-imidazo[4,5-c]pyridin-2-yl compounds, the use of such compounds as inhibitors of protein kinase B activity and in the treatment of cancer and arthritis.
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Page/Page column 64

(2008/06/13)

Mitsunobu coupling of nucleobases and alcohols: An efficient, practical synthesis for novel nonsugar carbon nucleosides
(Chemical Equation Presented) A simple facile synthesis of substituted purine derivatives has been developed by using Mitsunobu conditions for an alcohol and a respective nucleobase. A wide range of alcohols produces good to excellent yield (>90%). The resulting purine analogues show good regioselectivity with N-9 substitution as the dominant products in most of the cases. Application of diastereospecific alcohols reveals a complete inversion of the carbon stereogenic center giving a single diastereomer. More than two dozen novel nucleobase derivatives have been prepared in high yield.
Lu, Weibing,Sengupta, Sujata,Petersen, Jeffrey L.,Akhmedov, Novruz G.,Shi, Xiaodong
p. 5012 - 5015
(2008/02/07)

Catalytic activation of N-N multiple bonds: A homogeneous palladium catalyst for mechanistically unprecedented reduction of azo compounds
Just two oxidation states are involved in the homogeneous reduction of azo compounds at a single palladium catalyst site. The reaction proceeds through an intermediate state in which the catalyst displays a novel palladadiaziridine structure, and ethanol or related alcohols can be employed as the terminal reducing agent (see scheme). (Chemical Equation Presented).
Muniz, Kilian,Nieger, Martin
p. 2305 - 2308
(2007/10/03)

BENZAMIDE DERIVATIVES AND THEIR USE AS GLUCOKINASE ACTIVATING AGENTS
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Page/Page column 73

(2008/06/13)

BENZOYL AMINO PYRIDYL CARBOXYLIC ACID DERIVATIVES USEFUL AS GLUCOKINASE (GLK) ACTIVATORS
Compounds of Formula: (I); wherein: R1 is selected from: fluoro, chloro, C1-3alkyl and C1-3alkoxy; R2-X- is selected from: methyl, methoxymethyl and Formula: (X); n is 0,1 or 2; or a salt, pro-drug or solvate thereof are described. Their use as GLK activators, pharmaceutical compositions containing them, and processes for their preparation are also described.
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Page/Page column 26-27

(2010/02/12)

PROLINE DERIVATIVES HAVING AFFINITY FOR THE CALCIUM CHANNEL ALPHA-2-DELTA SUBUNIT
The compounds of formula (I) or a pharmaceutically acceptable salt, solvate or pro-drug thereof, are proline derivatives useful in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, fibromyalgia, arthritis, neuropathalogical disorders, sleep disorders, visceral pain disorders and gastrointestinal disorders. Processes for the preparation of the final products and intermediates useful in the process are included. Pharmaceutical compositions containing one or more of the compounds are also included. Wherein either X is O, S, NH or CH2 and Y is CH2 or a direct bond, or Y is O, S or NH and X is CH2; and R is a 3-12 membered cycloalkyl, 4-12 membered heterocycloalkyl, heteroaryl or aryl, where any ring may be optionally substituted with one or more substituents independently selected from halogen, hydroxy, cyano, nitro, amino, hydroxycarbonyl, Cl-C6 alkyl, Cl-C6 alkenyl, CI-C6 alkynyl, Cl-C6 alkoxy, hydroxyC,-C6 alkyl, Cl-C6 alkoxyC,-C6 alkyl, perfluoro Cl-C6 alkyl, perfluoroC,-C6 alkoxy, Cl-C6 alkylamino, di- C1-C6 alkylamino, aminoC1-C6 alkyl, Cl-C6 alkylaminoC,-C6 alkyl, di-Cl-C6 alkylaminoC,-C6 alkyl, CI-C6acyl, C1-C6acyloxy, Cl-C6acyloxyC,-C6 alkyl, Cl-C6 acylamino, Cl-C6 alkylthio, C1-C6 alkylthiocarbonyl, C1-C6 alkylthioxo, C1-C6 alkoxycarbonyl, Cl-C6 alkylsulfonyl, C1-C6 alkylsulfonylamino, aminosulfonyl, Cl-C6 alkylaminosulfonyl, di-Cl-C6 alkylaminosulfonyl, 3-8 membered cycloalkyl, 4-8 membered heterocycloalkyl, phenyl and monocyclic heteroaryl; or a pharmaceutically acceptable salt, solvate or pro-drug thereof.
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Page/Page column 66-67

(2010/02/06)

PROCESS FOR THE ENANTIOSELECTIVE SYNTHESIS OF PROPARGYL ALCOHOL DERIVATIVES OF R CONFIGURATION FROM THE RACEMIC MIXTURES THEREOF
The invention relates to a novel process for synthesizing organic compounds of general Formula (I). The said process may be carried out on an industrial scale and makes it possible to obtain from a mixture of racemic alcohols of formula (II), the corresponding chiral alcohols of R configuration, in a high chemical yield.
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Page/Page column 18

(2008/06/13)

An improved synthesis of azidothymidine
A convenient and high yielding procedure is described for a direct conversion of thymidine (1) into 2,3'-anhydrothymidine (2) using the Mitsunobu reaction. Isolation and characterization of two new compounds, 3 and 4, are discussed. AZT has been synthesized from 1 in two steps, in 62% overall yield, by heating 2 with NaN3 in DMF.
Balagopala, Meher I.,Ollapally, Abraham P.,Lee, Henry J.
p. 899 - 906
(2007/10/03)

Diels-Alder Reaction of Dialkyl Diazenedicarboxylates with Perylenes; A New Synthesis of Polycyclic Aromatic Pyridazines
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Tokita, Sumio,Hiruta, Kimihiro,Kitahara, Kiyoshi,Nishi, Hisao
p. 229 - 231
(2007/10/02)