1198575-41-5Relevant academic research and scientific papers
Rh(III)?catalyzed synthesis of isoquinolines from N-hydroxyoximes and alkynes in γ-valerolactone
Jiang, Kuan-Chang,Wang, Liang,Chen, Qun,He, Ming-Yang,Shen, Ming-Gui,Zhang, Zhi-Hui
, p. 94 - 102 (2021)
A Rh (III)?catalyzed synthesis of isoquinoline derivatives from N-hydroxyoximes and alkynes via C–H activation/annulation process in biomass-derived γ-valerolactone (GVL) has been developed. A series of functional groups were well tolerated, affording the desired products in good to excellent yields.
Hydroxylamine-O-Sulfonic Acid (HOSA) as a Redox-Neutral Directing Group: Rhodium Catalyzed, Additive Free, One-Pot Synthesis of Isoquinolines from Arylketones
Biswal, Pragati,Pati, Bedadyuti Vedvyas,Chebolu, Rajesh,Ghosh, Asit,Ravikumar
, p. 1006 - 1014 (2020/02/15)
A new application of hydroxylamine-O-sulfonic acid (HOSA) has been discovered whereby aromatic ketones react with HOSA and alkynes to form isoquinolines in the presence of a RhIII catalyst. This C–H/N–O annulation methodology gives excellent yields even without any silver additive, acid/base or metal oxidant. This is the first report wherein a directing group is simultaneously forming in situ, acting as acid additive, and also as an internal oxidant.
Cp*Co(iii)-catalyzed annulation of azines by C-H/N-N bond activation for the synthesis of isoquinolines
Deshmukh, Dewal S.,Yadav, Prashant A.,Bhanage, Bhalchandra M.
, p. 3489 - 3496 (2019/04/14)
Herein, an efficient, atom economic and external oxidant free approach has been disclosed for the synthesis of isoquinolines. Azines were employed for annulation reactions with alkynes via sequential C-H/N-N bond activation using an air-stable cobalt catalyst. The method takes advantage of the incorporation of both the nitrogen atoms of azines into the desired isoquinoline products, offering the highest atom economy. In addition, the developed protocol works under external oxidant as well as silver salt free conditions. Furthermore, the established methodology features a relatively broad substrate scope with high product yields and scalability up to the gram level.
Rapid and Atom Economic Synthesis of Isoquinolines and Isoquinolinones by C–H/N–N Activation Using a Homogeneous Recyclable Ruthenium Catalyst in PEG Media
Deshmukh, Dewal S.,Gangwar, Neha,Bhanage, Bhalchandra M.
, p. 2919 - 2927 (2019/05/10)
Herein, we report an atom-efficient, rapid, green, and sustainable approach to synthesize isoquinolines and isoquinolinones using a homogeneous recyclable ruthenium catalyst in PEG Media assisted by microwave energy. Dibenzoylhydrazine was used for C–H/N–N activation reactions for the first time in combination with ketazine as oxidizing directing groups for annulation reactions with internal alkynes. The developed protocol is environmentally benign due to significantly shortened times with an easy extraction method, higher atom economy, external oxidant and silver or antimony salt free conditions, applicability to a gram scale synthesis, use of biodegradable solvent and wide substrate scope with higher product yields. Moreover, it is worth noting that the established methodology allowed reuse of the catalytic system for up to five successive runs with minimal loss in activity.
Cp*Co(III) catalyzed annulation of N-Cbz hydrazones for the redox-neutral synthesis of isoquinolines via C–H/N–N bond activation
Subhedar, Dnyaneshwar D.,Deshmukh, Dewal S.,Bhanage, Bhalchandra M.
, p. 3121 - 3130 (2019/08/30)
A new cascade oxidative cyclization reaction of N-Cbz hydrazones with internal alkynes has been explored for the preparation of isoquinoline derivatives using Cp*CoIII-catalyst through C–H and N–N bond functionalization. N-Cbz hydrazones are ra
Ruthenium-Catalyzed Annulation of N -Cbz Hydrazones via C-H/N-N Bond Activation for the Rapid Synthesis of Isoquinolines
Bhanage, Bhalchandra M.,Deshmukh, Dewal S.
, p. 2506 - 2514 (2019/06/08)
In this work, N -Cbz hydrazone has been employed as a rarely explored directing group for the synthesis of isoquinolines by annulation with internal alkynes via C-H/N-N activation using Ru catalyst. Additive as well as external oxidant-free rapid protocol
Easy access to synthesize isoquinolines from aryl ketoximes and internal alkynes via Iridium (III)-catalyzed C[sbnd]H/N[sbnd]O bond activation
Lin, Wei,Hu, Xiu-Xiu,Zhuang, Cang-Wei,Wang, Ya-Zhen
, p. 3015 - 3023 (2019/04/30)
A highly efficient approach to synthesize isoquinoline derivatives through Iridium(III)-catalyzed cyclization of aryl ketoximes and internal alkynes without oxidant is reported. A broad range isoquinolines are obtained in good to excellent yields and various functional groups are well tolerated.
N-Tosylhydrazone directed annulation via C-H/N-N bond activation in Ru(ii)/PEG-400 as homogeneous recyclable catalytic system: a green synthesis of isoquinolines
Deshmukh, Dewal S.,Bhanage, Bhalchandra M.
, p. 4864 - 4873 (2018/07/15)
A green and sustainable methodology for the synthesis of isoquinolines using Ru(ii)/PEG-400 as a homogeneous recyclable catalytic system has been demonstrated. N-Tosylhydrazone, a rarely explored directing group, has been successfully employed for an annu
Novel polysubstitution isoquinoline derivative and synthesis method thereof
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Paragraph 0021; 0030; 0031, (2018/03/01)
The invention provides a novel polysubstitution isoquinoline derivative shown as a formula (I) and a synthesis method thereof. The formula I is shown in the specification. A C-H activation/cyclization method is used; ketoxime and diphenylacetypene are used as raw material; pentamethyl cyclopentadiene iridochloride is used as a catalyst for synthesizing the isoquinoline derivative. The preparation method is simple; the catalyst consumption is low; the reaction conditions are mild; the reaction steps are few; the reaction time is short; the yield is high. The isoquinoline derivative provided by the invention belongs to a kind of alkaloid compounds with important medicine activity, and can be widely applied to the study in aspects of fields of medicine and agriculture.
Cobalt(III)-Catalyzed Dehydrative [4+2] Annulation of Oxime with Alkyne by C-H and N-OH Activation
Sen, Malay,Kalsi, Deepti,Sundararaju, Basker
, p. 15529 - 15533 (2015/11/03)
Efficient, scalable cobalt-catalyzed redox-neutral [4+2] annulation of readily available oximes and alkyne is reported. The developed synthetic methodology is widely applicable and tolerates various functional groups including heterocycles. A stable CpCoIII neutral complex is employed as the catalyst for this redox-neutral [4+2] annulation reaction, which progresses smoothly by way of a reversible cyclometallation without any external oxidizing agent, and produces only water as the side product.
