879-15-2Relevant articles and documents
Rh(II)-catalyzed formal [3+3] cycloaddition of diazonaphthoquinones and propargyl alcohols: Synthesis of 2,3-dihydronaphtho-1,4-dioxin derivatives
Kitamura, Mitsuru,Nishimura, Tomoaki,Otsuka, Kota,Shimooka, Hirokazu,Okauchi, Tatsuo
supporting information, (2020/03/27)
A Rh(II)-catalyzed formal [3+3] cyclization of diazonaphthoquinones and propargyl alcohol is reported to afford 2,3-dihydro-1,4-benzodioxins. Various terminal propargyl alcohols react with diazonapthoquinone in the presence of Rh2(OAc)4/s
ELECTROPHILIC AZIDIZING AGENT OR DIAZOTIZING AGENT
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Paragraph 0082-0083, (2019/07/31)
PROBLEM TO BE SOLVED: To provide a novel electrophilic azidizing agent that is safe without explosibility, capable of azidizing a nucleophilic compound in an electrophilic manner. SOLUTION: The present invention provides an azide imidazolium derivative re
A 'sulfonyl-azide-free' (SAFE) aqueous-phase diazo transfer reaction for parallel and diversity-oriented synthesis
Dar'In, Dmitry,Kantin, Grigory,Krasavin, Mikhail
supporting information, p. 5239 - 5242 (2019/05/08)
Diazo transfer reactions are notoriously associated with the use of potentially explosive sulfonyl azides. The first 'sulfonyl-azide-free' (SAFE) protocol for producing diazo compounds from their active-methylene precursors via the Regitz diazo transfer reaction was developed and has displayed a remarkable substrate scope. It can be applied to generating arrays of diazo compounds for further evolution via combinatorial chemistry and a range of scaffold-generating transformations.
Rh(iii)-Catalyzed straightforward arylation of 8-methyl/formylquinolines using diazo compounds
Ghosh, Bidhan,Samanta, Rajarshi
supporting information, p. 6886 - 6889 (2019/06/18)
A straightforward Rh(iii)-catalyzed general strategy was developed for the introduction of naphthol/phenol moieties to the C(sp3)-H bond of 8-methylquinoline using diazonaphthalen-2(1H)-ones/quinone diazides. The developed method was further extended towards the arylation of 8-formylquinolines to accomplish diarylketone derivatives. The method is simple, relatively rapid, and chemo and regioselective with a wide scope and functional group tolerance. The synthetic utility was established through gram-scale synthesis and biologically active molecule construction.
Ir(III)-catalyzed direct C-H functionalization of arylphosphine oxides: A strategy for MOP-type ligands synthesis
Liu, Zhong,Wu, Ji-Qiang,Yang, Shang-Dong
supporting information, p. 5434 - 5437 (2017/11/06)
Diazo compounds as coupling partners are efficiently applied to Ir(III)-catalyzed direct C-H functionalization of arylphos-phine oxides. Involving C-H activation, carbene insertion, and tautomerism, this reaction proceeds under mild conditions, thus proving an approach to the synthesis of MOP-type ligand precursor in a single step. The utility of this transformation has been further demonstrated in ligand synthesis as well as in the construction of phosphole framework.
Synthesis of diazonaphthoquinones from naphthols by diazo-transfer reaction
Kitamura, Mitsuru,Sakata, Rie,Tashiro, Norifumi,Ikegami, Azusa,Okauchi, Tatsuo
, p. 824 - 833 (2015/06/25)
Various orthodiazonaphthoquinones (1-diazo-2(1H)-naphthalenones and 2-diazo-1(2H)-naphthalenones) were synthesized using the diazo-transfer reaction between the appropriate naphthol and 2-azido-1,3-dimethylimidazolinium chloride (ADMC). The ADMC was prepa
3-Naphthylindole Construction by Rhodium(II)-Catalyzed Regioselective Direct Arylation of Indoles with 1-Diazonaphthalen-2-(1H)-ones
Baral, Ek Raj,Lee, Yong Rok,Kim, Sung Hong
, p. 2883 - 2892 (2015/09/28)
The regioselective direct 3-arylation of indoles with 1-diazonaphthalen-2-(1H)-ones was developed by means of a rhodium(II) pivalate-catalyzed cross-coupling reaction. This procedure provided a variety of novel 3-naphthylindoles in high yield. The direct coupling of benzofuran, pyrrole or furan with 1-diazonaphthalen-2-(1H)-ones afforded 2- or 3-naphthyl substituted heterocycles.
Pd(OAc)2-catalyzed macrocyclization of 1,2-diazonaphthoquinones with cyclic ethers
Kitamura, Mitsuru,Kisanuki, Masato,Kanemura, Koichi,Okauchi, Tatsuo
supporting information, p. 1554 - 1557 (2014/04/17)
Pd(OAc)2 was found to be an efficient catalyst for the macrocyclization of 1,2-diazonaphthoquinones and cyclic ethers. This transformation serves as an efficient method for the synthesis of protected 1,2-naphthalenediols.
Synthesis of 1,2-naphthalenediol diacetates by rhodium(II)-catalyzed reaction of 1,2-diazonaphthoquinones with acetic anhydride
Kitamura, Mitsuru,Kisanuki, Masato,Okauchi, Tatsuo
supporting information; scheme or table, p. 905 - 907 (2012/03/27)
A metal-catalyzed reaction of α-diazocarbonyl compounds with an acid anhydride is reported. In particular, 1,2-naphthalenediol diacetates were synthesized by the reaction of 1,2-diazonaphthoquinones with acetic anhydride catalyzed by Rh2(OAc)s
Synthesis of diazonaphthoquinones from naphthols by diazo-transfer reaction with 2-azido-1,3-dimethylimidazolinium chloride
Kitamura, Mitsuru,Tashiro, Norifumi,Sakata, Rie,Okauchi, Tatsuo
experimental part, p. 2503 - 2505 (2010/12/18)
An efficient synthetic method for the synthesis of diazonaphthoquinones from naphthols is described. A variety of diazonaphthoquinones were synthesized from the corresponding naphthols by the diazo transfer with 2-azido-1,3- dimethylimidazolinium chloride prepared by the reaction of 2-chloro-1,3- dimethylimidazorinium chloride and sodium azide. Georg Thieme Verlag Stuttgart New York.