- Clickable azide-functionalized bromoarylaldehydes – synthesis and photophysical characterization
-
Herein, we present a facile synthesis of three azide-functionalized fluorophores and their covalent attachment as triazoles in Huisgen-type cycloadditions with model alkynes. Besides two ortho- and para-bromo-substituted benzaldehydes, the azide functionalization of a fluorene-based structure will be presented. The copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) of the so-synthesized azide-functionalized bromocarbaldehydes with terminal alkynes, exhibiting different degrees of steric demand, was performed in high efficiency. Finally, we investigated the photophysical properties of the azide-functionalized arenes and their covalently linked triazole derivatives to gain deeper insight towards the effect of these covalent linkers on the emission behavior.
- Friedrich, Marius,G?bel, Dominik,Lork, Enno,Nachtsheim, Boris J.
-
supporting information
p. 1683 - 1692
(2021/06/25)
-
- Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes
-
A highly efficient palladium-catalyzed arylation of azoles at the C2-position using 1-aryltriazenes as aryl reagents was developed. Azoles including oxazoles, thiazoles, imidazoles, 1,3,4-oxadiazoles, and oxazolines could react with 1-aryltriazenes smoothly to generate the corresponding products in good to excellent yields, and various substitution patterns were tolerated toward the reaction.
- Liu, Can,Wang, Zhiming,Wang, Lei,Li, Pinhua,Zhang, Yicheng
-
p. 9209 - 9216
(2019/11/05)
-
- Aerobic C(sp2)-H Hydroxylations of 2-Aryloxazolines: Fast Access to Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores
-
The direct hydroxylation of 2-aryloxazolines via a deprotonative magnesiation using TMPMgCl·LiCl and subsequent oxidation with molecular oxygen or air as a green oxidant is reported. This method proceeds under mild conditions at room temperature with high regioselectivity and chemoselectivity. The obtained phenols exhibit tunable luminescence properties, induced by excited-state intramolecular proton transfer. This method opens a new opportunity for the sustainable synthesis of luminescent organic molecules.
- G?bel, Dominik,Clamor, Nils,Lork, Enno,Nachtsheim, Boris J.
-
supporting information
p. 5373 - 5377
(2019/06/07)
-
- Regioselective: Ortho -functionalization of bromofluorenecarbaldehydes using TMPMgCl·LiCl
-
A highly regioselective functionalization of 7-bromofluorene-2-carbaldehydes, potent organic chromophores, in position C3 using a mild ortho-metallation strategy (DoM) with TMPMgCl·LiCl has been developed. This approach allows the preparation of highly functionalized fluorene derivatives by conversion of the in situ generated metalated species with various electrophiles giving a fast access to novel organic phosphorescent dyes.
- G?bel, Dominik,Clamor, Nils,Nachtsheim, Boris J.
-
supporting information
p. 4071 - 4075
(2018/06/12)
-
- Secondary Phosphine Oxide Preligands for Palladium-Catalyzed C–H (Hetero)Arylations: Efficient Access to Pybox Ligands
-
C–H arylations of oxazolines were accomplished with a well-defined palladium catalyst derived from a secondary bisdiamantyl phosphine oxide. The single-component secondary phosphine oxide (SPO)-palladium complex enabled C–H activations with aryl bromides
- Ghorai, Debasish,Müller, Valentin,Keil, Helena,Stalke, Dietmar,Zanoni, Giuseppe,Tkachenko, Boryslav A.,Schreiner, Peter R.,Ackermann, Lutz
-
supporting information
p. 3137 - 3141
(2017/09/06)
-
- Palladium-catalyzed electrophilic C–H fluorination of arenes using oxazoline as a removable directing group
-
Dimethyloxazoline was rationally designed to act as a removable ortho-directing group (DG) for the palladium-catalyzed C–H electrophilic fluorination of arenes. Using NFSI as the fluorinating agent, and Pd(II), Ag(I) catalytic system, electrophilic C(sp2–H) ortho-fluorination took place on a variety of aryl substrates to afford the corresponding mono- and di-fluorinated products.
- Gutierrez, David A.,Lee, Wan-Chen Cindy,Shen, Yuning,Li, Jie Jack
-
supporting information
p. 5372 - 5376
(2016/11/11)
-
- Manganese-Catalyzed Direct Nucleophilic C(sp2)-H Addition to Aldehydes and Nitriles
-
Herein, a manganese-catalyzed nucleophilic addition of inert C(sp2)-H bonds to aldehydes and nitriles is disclosed by virtue of a dual activation strategy. The reactions feature mild reaction conditions, excellent regio- and stereoselectivity, and a wide substrate scope, which includes both aromatic and olefinic C-H bonds, as well as a large variety of aldehydes and nitriles. Moreover, mechanistic studies shed light on possible catalytic cycles.
- Zhou, Bingwei,Hu, Yuanyuan,Wang, Congyang
-
supporting information
p. 13659 - 13663
(2015/11/16)
-
- Analogues of doxanthrine reveal differences between the dopamine D 1 receptor binding properties of chromanoisoquinolines and hexahydrobenzo[a]phenanthridines
-
Efforts to develop selective agonists for dopamine D1-like receptors led to the discovery of dihydrexidine and doxanthrine, two bioisosteric β-phenyldopamine-type full agonist ligands that display selectivity and potency at D1-like receptors. We report herein an improved methodology for the synthesis of substituted chromanoisoquinolines (doxanthrine derivatives) and the evaluation of several new compounds for their ability to bind to D1- and D2-like receptors. Identical pendant phenyl ring substitutions on the dihydrexidine and doxanthrine templates surprisingly led to different effects on D1-like receptor binding, suggesting important differences between the interactions of these ligands with the D1 receptor. We propose, based on the biological results and molecular modeling studies, that slight conformational differences between the tetralin and chroman-based compounds lead to a shift in the location of the pendant ring substituents within the receptor.
- Cueva, Juan Pablo,Chemel, Benjamin R.,Juncosa Jr., Jose I.,Lill, Markus A.,Watts, Val J.,Nichols, David E.
-
scheme or table
p. 97 - 107
(2012/03/22)
-
- C-H bond arylations and benzylations on oxazol(in)es with a palladium catalyst of a secondary phosphine oxide
-
An air-stable, well-defined palladium complex derived from secondary phosphine oxide (SPO) (1-Ad)2P(O)H enabled efficient C-H bond functionalizations with ample scope, which set the stage for direct arylations and benzylations of (benz)oxazoles, as well as unprecedented palladium-catalyzed C-H bond arylations on nonaromatic oxazolines.
- Ackermann, Lutz,Barfuesser, Sebastian,Kornhaass, Christoph,Kapdi, Anant R.
-
supporting information; experimental part
p. 3082 - 3085
(2011/08/07)
-
- A novel and direct synthesis of 1,3,4-oxadiazoles or oxazolines from carboxylic acids using cyanuric chloride/indium
-
Direct synthesis of various oxazolines and 1,3,4-oxadiazoles from carboxylic acids was achieved using cyanuric chloride/indium under very mild conditions.
- Kangani, Cyrous O.,Day, Billy W.
-
experimental part
p. 5332 - 5335
(2009/12/06)
-
- Open vessel mode microwave-assisted synthesis of 2-oxazolines from carboxylic acids
-
Microwave-assisted synthesis of 2-oxazolines from carboxylic acids using the open vessel technique is described. This efficient method involves direct condensation of carboxylic acids with excess 2-amino-2-methyl-1-propanol at 170 °C to give the corresponding 2-oxazolines in moderate to excellent yields.
- Sharma, Rishi,Vadivel, Subramanian K.,Duclos Jr., Richard I.,Makriyannis, Alexandros
-
experimental part
p. 5780 - 5782
(2009/12/26)
-
- TRANS-FUSED CHROMENOISOQUINOLINES SYNTHESIS AND METHODS FOR USE
-
Optionally substituted chromenoisoquinolines and analogs and derivatives thereof are described herein. In addition, syntheses of these compounds are described herein. In addition, uses of these compounds as dopamine receptor binding compounds are described herein.
- -
-
Page/Page column 15
(2009/02/11)
-
- One pot direct synthesis of amides or oxazolines from carboxylic acids using Deoxo-Fluor reagent
-
A mild and highly efficient one pot-one step condensation and/or condensation-cyclization of various acids to amides and/or oxazolines using Deoxo-Fluor reagents is described. Parallel syntheses of various free fatty acids with 2-amino-2,2-dimethyl-1-propanol resulted with excellent yields.
- Kangani, Cyrous O.,Kelley, David E.
-
p. 8917 - 8920
(2007/10/03)
-
- Facile Syntheses of Oxazolines and Thiazolines with N-Acylbenzotriazoles under Microwave Irradiation
-
Microwave reactions of 2-amino-2-methyl-1-propanol (2) or 2-aminoethanethiol hydrochloride (4) with readily available N-acylbenzotriazoles 1a-j in the presence of SOCl2 produced 2-substituted 2-oxazolines 3a-j in 84-98% yields and 2-substituted
- Katritzky, Alan R.,Cai, Chunming,Suzuki, Kazuyuki,Singh, Sandeep K.
-
p. 811 - 814
(2007/10/03)
-
- Direct synthesis of 2-oxazolines from carboxylic acids using 2-chloro-4,6-dimethoxy-1,3,5-triazine under mild conditions
-
2-Acyloxy-4,6-dimethoxy-1,3,5-triazines obtained from carboxylic acids and 2-chloro-4,6-dimethoxy-1,3,5-triazine were subsequently treated with 2-amino-2-methyl-1-propanol to afford the corresponding 2-oxazolines in excellent yield at room temperature.
- Bandgar,Pandit
-
p. 2331 - 2333
(2007/10/03)
-
- Pd(OAc)2/2-aryl-2-oxazolines catalyzed Suzuki coupling reactions of aryl bromides and arylboronic acids
-
A series of 2-aryl-2-oxazolines were prepared and examined as ligands for the Suzuki coupling reaction of aryl bromides and arylboronic acids. 2,2′-(1,3-Phenylene)bisoxazoline/Pd(OAc)2 was found to be an efficient catalyst for a variety of substrates to afford the coupling products in good to excellent yields.
- Tao, Bin,Boykin, David W
-
p. 4955 - 4957
(2007/10/03)
-
- Natural Kaolinitic clay catalyzed conversion of nitriles to 2-oxazolines
-
Natural Kaolinitic clay has been found effective as catalyst in the conversion of aromatic and aliphatic nilriles with 1,2-aminoalcohol to 2-oxazolines (56-96%, yield).
- Jnaneshwara,Deshpande,Lalithambika,Ravindranathan,Bedekar
-
p. 459 - 462
(2007/10/03)
-
- Phenacenes: A family of graphite ribbons. 2. Syntheses of some [7]phenacenes and an [11]phenacene by stilbene-like photocyclizations
-
It is proposed that members of the family of polycyclic aromatic compounds with an extended phenanthrene-like structural motif be designated as [n]phenacenes, where n is the number of fused benzene rings. [n]Phenacene molecules are related to layers of gr
- Mallory, Frank B.,Butler, Kelly E.,Evans, Amanda C.,Brondyke, Emilie J.,Mallory, Clelia W.,Yang, Changqing,Ellenstein, Aviva
-
p. 2119 - 2124
(2007/10/03)
-
- Palladium-Catalyzed Coupling of Oxazol-2-yl and 2-Oxazolin-2-yltrimethylstannanes with Aromatic Halides. A New Entry to 2-Aryl and 2-Heteroaryl Oxazoles and Oxazolines
-
4-Methyloxazole and 4,4-dimethyl-2-oxazoline were treated with n-butyllithium and trimethyltin chloride to give the corresponding 2-trimethylstannyl derivatives which in the presence of tetrakis(triphenylphosphine)palladium(0) as a catalyst undergo cross-
- Dondoni, Alessandro,Fantin, Giancarlo,Fogagnolo, Marco,Medici, Alessandro,Pedrini, Paola
-
p. 693 - 696
(2007/10/02)
-
- New Synthesis of 2-Substituted 2-Oxazolines: Transition-Metal-Catalyzed Cross-Coupling of Grignards with 2-(Methylthio)-4,4-dimethyl-2-oxazoline
-
A new synthesis of 2-aryl-4,4-dimethyl-2-oxazolines (18a-e) using nickel- and palladium-phosphine complexes to catalyze cross-coupling of Grignard reagents 17 with 2-(methylthio)-4,4-dimethyl-2-oxazoline (16) is described.This reaction represents the firs
- Pridgen, Lendon N.,Killmer, Lewis B.
-
p. 5402 - 5404
(2007/10/02)
-