229-67-4Relevant academic research and scientific papers
Cu(II)-Catalyzed Construction of Heterobiaryls using 1-Diazonaphthoquinones: A General Strategy for the Synthesis of QUINOX and Related P,N Ligands
Biswas, Aniruddha,Pan, Subarna,Samanta, Rajarshi
supporting information, p. 1631 - 1636 (2022/03/14)
An efficient and straightforward method was developed for the synthesis of heterobiaryls using easily available N-oxides and diazonaphthoquinones under cheap Cu(II) catalysis. The developed method offered QUINOX and related congeners in a simple manner. A wide scope of important heterobiaryls was achieved with high site selectivity. The synthesized naphthols were transformed into the privileged related P,N ligands. Suitable resolution methods can directly afford the corresponding axially chiral heterobiaryls.
Regioselective Synthesis of Polycyclic and Heptagon-embedded Aromatic Compounds through a Versatile π-Extension of Aryl Halides
Fu, Wai Chung,Wang, Zheng,Chan, Wesley Ting Kwok,Lin, Zhenyang,Kwong, Fuk Yee
supporting information, p. 7166 - 7170 (2017/06/13)
A versatile π-extension reaction was developed based on the three-component cross-coupling of aryl halides, 2-haloarylcarboxylic acids, and norbornadiene. The transformation is driven by the direction and subsequent decarboxylation of the carboxyl group, while norbornadiene serves as an ortho-C?H activator and ethylene synthon via a retro-Diels–Alder reaction. Comprehensive DFT calculations were performed to account for the catalytic intermediates.
Light-induced carbocyclization of iodoalkenes
Campos-Gómez, Esther,Campos, Pedro J.,González, Héctor F.,Rodríguez, Miguel A.
experimental part, p. 4292 - 4295 (2012/07/16)
The direct irradiation of iodoalkenes leads to the formation of carbon-centered radical by homolysis of the C-I bond. The photoreaction is used in cyclizations with formation of six membered rings.
A general and efficient method for the synthesis of benzo-(iso)quinoline derivatives
Mamane, Victor,Lou?rat, Frédéric,Iehl, Julien,Abboud, Mohamed,Fort, Yves
, p. 10699 - 10705 (2008/12/23)
A new, short and efficient synthesis of substituted benzo-(iso)quinoline derivatives is reported. The methodology is based on a Suzuki or Negishi cross-coupling followed by a cyclization reaction induced by t-BuOK in DMF to form the central ring. This approach allowed the synthesis of all four benzo-(iso)quinoline isomers and the substitution of each ring of the benzo-(iso)quinoline core.
Preparation of polycyclic azaarenes by an extended Pomeranz-Fritsch procedure
Hewlins, Michael J. E.,Salter, Rhys
, p. 2157 - 2163 (2008/03/28)
An extension of the Pomeranz-Fritsch procedure has been evaluated as a route to some polycyclic azaarenes. Aromatic aldehydes were treated with the dimethyl and diethyl acetals of 2-aminoethanal, the resulting imines reduced to amines which were tosylated and the resulting sulfonamides treated under a range of acidic conditions. The two naphthaldehydes led to benzo[f]isoquinoline and benzo[h]isoquinoline in overall yields of 13% and 36%. Phenanthrene-9- carbaldehyde and phenanthrene-3-carbaldehyde gave dibenzo[f,h]isoquinoline and naphtho[2,1-g]isoquinoline, respectively, as the major tetracyclic products. No pentacyclic product was obtained from a similar sequence starting from pyrene-1-carbaldehyde. Georg Thieme Verlag Stuttgart.
Model reactions for the synthesis of azacorannulenes and related heteroaromatic compounds
Dix, Ina,Doll, Christian,Hopf, Henning,Jones, Peter G.
, p. 2547 - 2556 (2007/10/03)
4-(2-Ethynylphenyl)pyridine (10), 3-(2-ethynylphenyl)pyridine (11), 2-(2-trimethylsilylethynylphenyl)pyridine (26), and 3-ethynyl-2-phenylpyridine (13) were prepared from readily available pyridine precursors by standard coupling reactions. Pyrolysis of 10 at 810 °C/0.5 Torr provided benzo[f]isoquinoline (45) and the benzopentalene dimer 47. Pyrolysis of 11 (820 °C/0.5 Torr) afforded benzo[f]quinoline (50), benzo[h]i-soquinoline (52), and a mixture of isomers of 47. Pyrolysis of 13 (820 °C/0.3 Torr) provided benzo[h]quinoline (56) and the novel azulene derivative azuleno[1,2-b]pyridine (58). When 26 was desilylated by treatment with TBAF in THF/water, the unusual "dimerization" product 37 was produced; its structure was confirmed by X-ray structural analysis. The mechanisms of these transformations are discussed. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
DEOXYGENATION OF TERTIARY AMINE N-OXIDES AND ARENE OXIDES BY IRON (II) PORPHYRIN AS A MODEL OF CYTOCHROME P-450 DEPENDENT REDUCTION
Miyata, Naoki,Santa, Tomofumi,Hirobe, Masaaki
, p. 377 - 380 (2007/10/02)
Tetraphenylporphiratoiron (II), a model complex of reduced cytochrome P-450, reduces several substrates such as tertiary amine N-oxides and arene oxides at room temperature in anaerobic conditions.A process for the direct oxene transfer from oxide to reduced iron porphyrin is suggested.KEYWORDS - cytochrome P-450; reduction; deoxygenation; tertiary amine N-oxide; tetraphenylporphinatoiron (II); oxene transfer; arene oxide; ferryl oxide
