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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 13, 1983 - Issue 6
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Original Articles

Convenient Synthesis of Indolines by Reduction of Indoles With Sodium Cyanoborohydride in Carboxylic Acids

Yatendra Kumar Department of CNS-Medicinal Chemistry, Astra Läkemedel AB, S-151 85, Södertälje, Sweden
&
Lennart Florvall Department of CNS-Medicinal Chemistry, Astra Läkemedel AB, S-151 85, Södertälje, Sweden
Pages 489-493 | Published online: 03 Jan 2007

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EmiliaR. Balogh, Bela Zsadon, Antal Csámpai & R. Pál. (1994) Reduction and N-Alkylation of α-Methylene-indolines with Sodium Cyanoborohydride in Carboxylic Acids. Synthetic Communications 24:5, pages 701-707.
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GordonW. Gribble & CharlesF. Nutaitis. (1985) SODIUM BOROHYDRIDE IN CARBOXYLIC ACID MEDIA. A REVIEW OF THE SYNTHETIC UTILITY OF ACYLOXYBOROHYDRIDES. Organic Preparations and Procedures International 17:4-5, pages 317-384.
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Jeremy R. Tuck, Lee E. Dunlap & David E. Olson. (2023) Synthetic Strategies toward Lysergic Acid Diethylamide: Ergoline Synthesis via α-Arylation, Borrowing Hydrogen Alkylation, and C–H Insertion. The Journal of Organic Chemistry.
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Zhongtao Yang, Xiai Luo, Zhipeng Zhang, Xiaoling Luo, Jia Zheng, Hui Luo & Weiguang Yang. (2022) Silver‐Catalyzed [3+2] Cycloaddition for the Diastereoselective Synthesis of anti ‐3‐Substituted Hydroindolin‐2‐Imines . Advanced Synthesis & Catalysis 364:24, pages 4433-4439.
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Dan Liu, Bin Shi, Hao Jiang, Ying Cheng, Wen-Jing Xiao & Liang-Qiu Lu. (2021) Synthesis of hydroindoles via desymmetric [3+2] cycloadditions of para -quinamines with photogenerated ketenes . Chemical Communications 57:68, pages 8496-8499.
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Aarushi Singh, Snigdha Singh, Shubham Sewariya, Nidhi Singh, Prashant Singh, Ajay Kumar, Rakeshwar Bandichhor & Ramesh Chandra. (2021) Stereospecific N-acylation of indoles and corresponding microwave mediated synthesis of pyrazinoindoles using hexafluoroisopropanol. Tetrahedron 84, pages 132017.
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Xiao-Yu Zhou & Xia Chen. (2021) Pd/C-Catalyzed transfer hydrogenation of N –H indoles with trifluoroethanol and tetrahydroxydiboron as the hydrogen source . Organic & Biomolecular Chemistry 19:3, pages 548-551.
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Hisham A. Maddah, Vikas Berry & Sanjay K. Behura. (2020) Biomolecular photosensitizers for dye-sensitized solar cells: Recent developments and critical insights. Renewable and Sustainable Energy Reviews 121, pages 109678.
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Brian Budke, Werner Tueckmantel, Kelsey Miles, Alan P. Kozikowski & Philip P. Connell. (2019) Optimization of Drug Candidates That Inhibit the D‐Loop Activity of RAD51. ChemMedChem 14:10, pages 1031-1040.
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Vishnu Ji Ram, Arun Sethi, Mahendra Nath & Ramendra Pratap. 2019. The Chemistry of Heterocycles. The Chemistry of Heterocycles 149 478 .
Richard C. LarockRichard C. Larock & Alexandre A. Pletnev. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 49 .
Huan Liu, Jian-Gang Chen, Chao Wang, Zhao-Tie Liu, Yang Li, Zhong-Wen Liu, Jianliang Xiao & Jian Lu. (2017) Immobilization of Cyclometalated Iridium Complex onto Multiwalled Carbon Nanotubes for Dehydrogenation of Indolines in Aqueous Solution. Industrial & Engineering Chemistry Research 56:40, pages 11413-11421.
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Kevin G. Liu, Jennifer R. Lo & Albert J. Robichaud. (2010) One-pot synthesis of highly substituted indolines. Tetrahedron 66:3, pages 573-577.
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Jumina, Naresh Kumar & David St.C. Black. (2009) Synthetic approaches to activated pyrrolo[3,2,1-hi]indoles: synthesis of 6,8-dimethoxy pyrrolo[3,2,1-hi]indole. Tetrahedron 65:12, pages 2591-2598.
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Lindsay A. HobsonWilliam A. NugentStephen R. AndersonSubodh S. DeshmukhJames J. Haley IIIPingli LiuNicholas A. MagnusPatrick SheeranJames P. SherbineBenjamin R. P. StoneJiang Zhu. (2007) The Synthesis of a 5HT 2C Receptor Agonist . Organic Process Research & Development 11:6, pages 985-995.
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Alain Merschaert, Pascal Boquel, Jean-Pierre Van Hoeck, Hugo Gorissen, Alfio Borghese, Benjamin Bonnier, Anne Mockel & Freddy Napora. (2006) Novel Approaches towards the LTD 4 /E 4 Antagonist, LY290154 . Organic Process Research & Development 10:4, pages 776-783.
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Ellen W. Baxter & Allen B. Reitz. 2004. Organic Reactions. Organic Reactions 1 714 .
R.J. Sundberg. 1996. Indoles. Indoles 145 158 .
Yoshio Nishimura. 1995. Stereoselective Synthesis (Part J). Stereoselective Synthesis (Part J) 75 121 .
Yoshio Nishimura, When-mei Wang, Toshiaki Kudo & Shinichi Kondo. (1992) Total Synthesis of Siastatin B and Its Enantiomer Using Carbohydrate as a Chiral Educt. Bulletin of the Chemical Society of Japan 65:4, pages 978-986.
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David W Brown, Paul R Graupner, Malcolm Sainsbury & Howard G Shertzer. (1991) New antioxidants incorporating indole and indoline chromophores. Tetrahedron 47:25, pages 4383-4408.
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Gordon W. Gribble. 1991. Comprehensive Organic Synthesis. Comprehensive Organic Synthesis 603 633 .
Daniel M. Ketcha & Brett A. Lieurance. (1989) The reduction of N-phenylsulfonyl)indoles with sodium cyanoborohydride in trifluoroacetic acid. Tetrahedron Letters 30:49, pages 6833-6836.
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Y. KUMAR & L. FLORVALL. (2016) ChemInform Abstract: CONVENIENT SYNTHESIS OF INDOLINES BY REDUCTION OF INDOLES WITH SODIUM CYANOBOROHYDRIDE IN CARBOXYLIC ACIDS. Chemischer Informationsdienst 14:42.
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