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Search results for: Bromoacetaldehyde

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#33335599   2020/11/30 To Up

Three-component reactions of aromatic amines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal to access -(hetero)aryl-4,5-unsubstituted pyrroles.

-(Hetero)aryl-4,5-unsubstituted pyrroles were synthesized from (hetero)arylamines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal by using aluminum(III) chloride as a Lewis acid catalyst through [1 + 2 + 2] annulation. This new versatile methodology provides a wide scope for the synthesis of different functional -(hetero)aryl-4,5-unsubstituted pyrrole scaffolds, which can be further derived to access multisubstituted pyrrole-3-carboxamides. In the presence of 1.2 equiv of KI, a polysubstituted pyrazolo[3,4-]pyridine derivative was also successfully synthesized.
Wenbo Huang, Kaimei Wang, Ping Liu, Minghao Li, Shaoyong Ke, Yanlong Gu

1170 related Products with: Three-component reactions of aromatic amines, 1,3-dicarbonyl compounds, and α-bromoacetaldehyde acetal to access -(hetero)aryl-4,5-unsubstituted pyrroles.

500 reactions100 reactions500 g5 reactions50 ug50 ug1 moduleOne 96-Well Strip Micropl100 ul100.00 ug50 ug100 mg

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#29978706   2018/07/06 To Up

Bismuth(III) Triflate Catalyzed Three-Component Reactions of Indoles, Ketones, and α-Bromoacetaldehyde Acetals Enable Indole-to-Carbazole Transformation.

A three-component reaction of indoles, α-bromoacetaldehyde acetals, and ketones was developed by using bismuth(III) triflate as the catalyst to realize a straightforward approach for synthesizing carbazole derivatives. The reaction was established mechanistically through the autotandem catalysis of Bi(OTf) in the following two steps: (i) Friedel-Crafts-type alkylation of indole with α-bromoacetaldehyde acetal, which produced a tryptaldehyde-type intermediate and (ii) [4 + 2] annulation of this intermediate with the ketone component.
Yanlong Gu, Wenbo Huang, Shaomin Chen, Xin Wang

1976 related Products with: Bismuth(III) Triflate Catalyzed Three-Component Reactions of Indoles, Ketones, and α-Bromoacetaldehyde Acetals Enable Indole-to-Carbazole Transformation.

5 reactions100 reactions100ug Lyophilized100 mg50 ug 5 reactions500 MG75 reactions1000 tests100 Reactions100ul

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#26481194   2015/10/20 To Up

Enantioselective Total Syntheses of (-)-Rhazinilam, (-)-Leucomidine B, and (+)-Leuconodine F.

A divergent total synthesis of three structurally distinct natural products from imine 9 was accomplished through an approach featuring: 1) a Pd-catalyzed decarboxylative cross-coupling, and 2) heteroannulation of 9 with bromoacetaldehyde and oxalyl chloride to give tetrahydroindolizine 6 and dioxopyrrole 7, respectively. The former was converted into (-)-rhazinilam, while the latter was converted into (-)-leucomidine B and (+)-leuconodine F. A substrate-directed highly diastereoselective reduction of a sterically unbiased double bond by using a homogeneous palladium catalyst was developed. A self-induced diastereomeric anisochronism (SIDA) phenomenon was observed for leucomidine B.
Dylan Dagoneau, Zhengren Xu, Qian Wang, Jieping Zhu

2706 related Products with: Enantioselective Total Syntheses of (-)-Rhazinilam, (-)-Leucomidine B, and (+)-Leuconodine F.

480/kit 5 GOne 96-Well Strip Micropl1 kit(96 Wells)2.5 mg100ug1x96 well plate1 kit10 mgOne 96-Well Strip Micropl1000 TESTS/0.65ml

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#25942416   2015/05/21 To Up

Occurrence and Comparative Toxicity of Haloacetaldehyde Disinfection Byproducts in Drinking Water.

The introduction of drinking water disinfection greatly reduced waterborne diseases. However, the reaction between disinfectants and natural organic matter in the source water leads to an unintended consequence, the formation of drinking water disinfection byproducts (DBPs). The haloacetaldehydes (HALs) are the third largest group by weight of identified DBPs in drinking water. The primary objective of this study was to analyze the occurrence and comparative toxicity of the emerging HAL DBPs. A new HAL DBP, iodoacetaldehyde (IAL) was identified. This study provided the first systematic, quantitative comparison of HAL toxicity in Chinese hamster ovary cells. The rank order of HAL cytotoxicity is tribromoacetaldehyde (TBAL) ≈ chloroacetaldehyde (CAL) > dibromoacetaldehyde (DBAL) ≈ bromochloroacetaldehyde (BCAL) ≈ dibromochloroacetaldehyde (DBCAL) > IAL > bromoacetaldehyde (BAL) ≈ bromodichloroacetaldehyde (BDCAL) > dichloroacetaldehyde (DCAL) > trichloroacetaldehyde (TCAL). The HALs were highly cytotoxic compared to other DBP chemical classes. The rank order of HAL genotoxicity is DBAL > CAL ≈ DBCAL > TBAL ≈ BAL > BDCAL>BCAL ≈ DCAL>IAL. TCAL was not genotoxic. Because of their toxicity and abundance, further research is needed to investigate their mode of action to protect the public health and the environment.
Clara H Jeong, Cristina Postigo, Susan D Richardson, Jane Ellen Simmons, Susana Y Kimura, Benito J Mariñas, Damia Barcelo, Pei Liang, Elizabeth D Wagner, Michael J Plewa

1008 related Products with: Occurrence and Comparative Toxicity of Haloacetaldehyde Disinfection Byproducts in Drinking Water.

50μl 100 G96/kit100 μg8 Sample Kit50 ug 100100 μg1 Set100 1 Set

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#25255205   2014/10/06 To Up

Synthesis of a library of propargylated and PEGylated α-hydroxy acids toward "clickable" polylactides via hydrolysis of cyanohydrin derivatives.

A new simple and practical protocol for scalable synthesis of a novel library of propargylated and PEGylated α-hydroxy acids toward the preparation of "clickable" polylactides was described. The overall synthesis starting from readily available propargyl alcohol, bromoacetaldehyde diethyl acetal, and OEGs or PEGs was developed as a convenient procedure with low cost and no need of column chromatographic purification. The terminal alkyne functionality survives from hydrolysis of the corresponding easily accessible cyanohydrin derivatives in methanolic sulfuric acid. Facile desymmetrization, monofunctionalization, and efficient chain-elongation coupling of OEGs further enable the incorporation of OEGs to α-hydroxy acids in a simple and efficient manner. At the end, synthesis of allyloxy lactic acid indicates that an alkene group is also compatible with the developed method.
Quanxuan Zhang, Hong Ren, Gregory L Baker

2341 related Products with: Synthesis of a library of propargylated and PEGylated α-hydroxy acids toward "clickable" polylactides via hydrolysis of cyanohydrin derivatives.

5 G 25 MG 5 G100 mg500 tests20ug100ug/vial5ml 100 G1 mg5 mg 100 G

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#24364699   2013/12/24 To Up

Modular synthesis of lamellarins via regioselective assembly of 3,4,5-differentially arylated pyrrole-2-carboxylates.

A modular synthesis of lamellarins via 3,4,5-differentially arylated pyrrole-2-carboxylate intermediates has been developed. The key reactions employed are Br-Li exchange-methoxycarbonylation of 2,5-dibromo-1-(tert-butoxycarbonyl)-1H-pyrrole (1) followed by palladium-catalyzed iterative Suzuki-Miyaura coupling of the pyrrole core. The 3,4,5-triarylpyrrole 4 thus synthesized was readily converted to 5,6-saturated lamellarin L (2) and 5,6-unsaturated lamellarin N (3) via lactonization followed by annulation of the pyrrole nitrogen and lateral aromatic ring at C5 using 2-bromoethyl phenyl sulfide or bromoacetaldehyde dimethyl acetal as two-carbon homologation agents. In principle, this strategy allows the production of diverse lamellarins in short steps with high yields using readily accessible arylboronic acids as aromatic modules.
Masashi Komatsubara, Teppei Umeki, Tsutomu Fukuda, Masatomo Iwao

2287 related Products with: Modular synthesis of lamellarins via regioselective assembly of 3,4,5-differentially arylated pyrrole-2-carboxylates.

5 G25 Rxns Kit100μg/vial100ug/vialBox of 10 vials for 480 m100ug/vial 5 G1 kit1000pcs100 ug/vial100 ug/vial

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#22909295   2012/08/21 To Up

Synthesis, characterization, and activity of yttrium(III) nitrate complexes bearing tripodal phosphine oxide and mixed phosphine-phosphine oxide ligands.

A series of four tripodal phosphine oxide ligands, (OPR(2))(2)CHCH(2)POR(2) (1a-1d), and four mixed phosphine-phosphine oxide ligands, (OPR(2))(2)CHCH(2)PR(2) (3a-3d), were synthesized and coordinated to yttrium to produce Y(NO(3))(3)[(OPR(2))(2)CHCH(2)POR(2)] (2a-2d) and Y(NO(3))(3)[(OPR(2))(2)CHCH(2)PR(2)](OPPh(3)) (4a-4d) complexes. The previously reported ligand 1a and unknown phosphine oxide ligands 1b-1d were generated in an unprecedented trisubstitution reaction of bromoacetaldehyde diethyl acetal, while the novel partially reduced ligands 3a-3d were synthesized from 1a-1d according to a known literature protocol for the selective monoreduction of bisphosphine oxides. The neutral yttrium complexes 2a-2d are nine-coordinate and display a tricapped trigonal-prismatic geometry. Complexes 4a-4d are also neutral, nine-coordinate species and have a pendant phosphine functionality, which provides the potential to form bimetallic early-late transition-metal complexes. Additionally, yttrium complexes 2a-2d were activated with base and tested for the ring-opening polymerization of ε-caprolactone, but the results showed that base by itself was significantly more effective than the yttrium species investigated.
Peter E Sues, Alan J Lough, Robert H Morris

2269 related Products with: Synthesis, characterization, and activity of yttrium(III) nitrate complexes bearing tripodal phosphine oxide and mixed phosphine-phosphine oxide ligands.

5 G200ul50 ug 25 mg1 mg11000 tests100ug 100 G25 mg 1 G10 mg

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#21815682   2011/08/18 To Up

Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

The Mukaiyama cross-aldol reaction of α-fluoro-, α-chloro-, and α-bromoacetaldehyde-derived (Z)-tris(trimethylsilyl)silyl enol ethers is described, furnishing anti-β-siloxy-α-haloaldehydes. A highly diastereoselective, one-pot, sequential double-aldol process is developed, affording novel β,δ-bissiloxy-α,γ-bishaloaldehydes. Reactions are catalyzed by C(6)F(5)CHTf(2) and C(6)F(5)CTf(2)AlMe(2) (0.5-1.5 mol %) and provide access to halogenated polyketide fragments.
Jakub Saadi, Matsujiro Akakura, Hisashi Yamamoto

2622 related Products with: Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

1000 ml 10 plates 25 G 250G200 ug 96 Tests 100 G100ug Lyophilized25 Rxns Kit10x50 ug 96 Tests

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#18004440   2007/09/10 To Up

A concise organocatalytic and enantioselective synthesis of isotetronic acids.

A concise enantioselective route to isotetronic acids using an organocatalyzed aldol reaction between alpha-oxocarboxylic acids and aldehydes has been developed, leading to the titled compounds in reasonable yields and good enantioselectivities.
Jean-Marc Vincent, Chrystèle Margottin, Muriel Berlande, Dominique Cavagnat, Thierry Buffeteau, Yannick Landais

1637 related Products with: A concise organocatalytic and enantioselective synthesis of isotetronic acids.

10 mg 5 G50 ug2.5 mg200ug100ug50 ug 1 mg1 ml100ul1,000 tests

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