1360651-35-9Relevant academic research and scientific papers
N-Iminopyridinium ylide-directed, cobalt-catalysed coupling of sp2C-H bonds with alkynes
Kwak, Se Hun,Daugulis, Olafs
supporting information, p. 11070 - 11073 (2020/10/05)
N-Iminopyridinium ylides are competent monodentate directing groups for cobalt-catalysed annulation of sp2C-H bonds with internal alkynes. The pyridine moiety in the ylide serves as an internal oxidant and is cleaved during the reaction. The annulation reactions possess excellent compatibility with heterocyclic substrates, tolerating furan, thiophene, pyridine, pyrrole, pyrazole, and indole functionalities.
Synthesis of isoquinolone via rhodium(III)-catalyzed C-H activation with 1,4,2-dioxazol-5-ones as oxidizing directing group
Zhu, Huajian,Zhuang, Rangxiao,Zheng, Wenya,Fu, Liping,Zhao, Yuanke,Tu, Luping,Chai, Yitao,Zeng, Linghui,Zhang, Chong,Zhang, Jiankang
, p. 3108 - 3112 (2019/05/08)
An efficient rhodium-catalyzed direct C-H activation for the synthesis of isoquinolone with 1,4,2-dioxazol-5-ones as oxidizing directing groups have been developed, which featured mild reaction conditions, short reaction time and satisfactory yield.
N-Sulfonylcarboxamide as an Oxidizing Directing Group for Ruthenium-Catalyzed C–H Activation/Annulation
Petrova, Elina,Rasina, Dace,Jirgensons, Aigars
, p. 1773 - 1779 (2017/04/13)
N-Sulfonylcarboxamides can act as both a directing group for C–H activation and an internal oxidant in the Ru-catalyzed annulation reaction with alkynes to give isoquinolones. Of all of the N-sulfonylcarboxamides that were studied, the N-(2,6-difluorophenyl)sulfonamide derivatives were found to be the most efficient and led to the formation of an unstable sulfinate byproduct that decomposed into 1,3-difluorobenzene under the reaction conditions. The described isoquinolone synthesis provides an alternative to the currently known traceless annulations of hydroxamic acid and sulfoximine derivatives.
Ru-Catalyzed One-Pot Diannulation of Heteroaryls: Direct Access to π-Conjugated Polycyclic Amides
Shankar, Majji,Ghosh, Koushik,Mukherjee, Kallol,Rit, Raja K.,Sahoo, Akhila K.
supporting information, p. 6416 - 6419 (2016/12/23)
A novel Ru-catalyzed oxidative double annulation of heteroarenes with symmetrical and unsymmetrical alkynes is reported. A general method for the unsymmetrical annulation of heteroarenes with two distinct alkynes is showcased for the first time. Methylphenyl sulfoximine (MPS) plays an important role in the annulations of heteroarenes and allows the construction of structurally complex π-conjugated heteroarene-fused polycyclic amide skeletons via the formation of multiple C-C and C-N bonds in a single operation. The reaction exhibits excellent substrate scope and tolerates a wide range of functional groups.
Cobalt-Catalyzed Cyclization of N-Methoxy Benzamides with Alkynes using an Internal Oxidant through C-H/N-O Bond Activation
Sivakumar, Ganesan,Vijeta, Arjun,Jeganmohan, Masilamani
supporting information, p. 5899 - 5903 (2016/04/26)
The cyclization of substituted N-methoxy benzamides with alkynes in the presence of an easily affordable cobalt complex and NaOAc provides isoquinolone derivatives in good to excellent yields. The cyclization reaction is compatible with a range of functio
Ruthenium(ii)-catalyzed C-H activation/C-N bond formation via in situ generated iminophosphorane as the directing group: Construction of annulated pyridin-2(1H)-ones
Arigela, Rajesh K.,Kumar, Ravi,Joshi, Trapti,Mahar, Rohit,Kundu, Bijoy
, p. 57749 - 57753 (2015/01/08)
We describe an efficient and straightforward synthesis of annulated pyridin-2(1H)-ones following condensation of acyl azides with internal alkynes via the ruthenium-catalyzed ortho C-H bond activation. The reaction in DCE proceeds via in situ generation of iminophosphoranes as directing group-coordination of Ru with N-atom-ortho cyclometallation-insertion of an alkyne into the Ru-C bond-protonation-reductive elimination in a domino sequence. The role and stability of in situ generated iminophosphorane and ruling out the possibility for the benzamide involvement was established using 1H and 31P NMR experiments. This journal is
Ruthenium-catalyzed aerobic oxidative cyclization of aromatic and heteroaromatic nitriles with alkynes: A new route to isoquinolones
Reddy, Mallu Chenna,Manikandan, Rajendran,Jeganmohan, Masilamani
supporting information, p. 6060 - 6062 (2013/07/19)
The oxidative cyclization of aromatic and heteroaromatic nitriles with alkynes in the presence of a catalytic amount of [{RuCl2(p-cymene)} 2], Cu(OAc)2·H2O and KPF6 in acetic acid under air gave isoquinolones in good to excellent yields.
A practical one-pot procedure for the synthesis of N-H isoquinolones
Lu, Shaonan,Lin, Yingfu,Zhong, Hongban,Zhao, Kang,Huang, Jianhui
supporting information, p. 2001 - 2005 (2013/04/23)
A practical one-pot procedure for the preparation of N-H isoquinolones has been developed. This 2-step process via C-H activation of N-alkoxyl benzamides and NaH-mediated dealkoxylation reaction has been demonstrated to be a high yielding alternative meth
Ruthenium-catalyzed isoquinolone synthesis through C-H activation using an oxidizing directing group
Li, Bin,Feng, Huiliang,Xu, Shansheng,Wang, Baiquan
supporting information; experimental part, p. 12573 - 12577 (2011/12/03)
The oxidant directs: A mild, practical, efficient, and regioselective Ru-catalyzed isoquinolone synthesis with a broad substrate scope was reported (see scheme). In this redox neutral process, the aromatic CiH bond functionalization can be performed at room temperature without using any external oxidant. The mechanism of the reaction was probed, and it was found that CiH activation is the turnover-limiting step.
