Practical Synthesis of Polysubstituted ImidazolesviaIodine- Catalyzed Aerobic Oxidative Cyclization of Aryl Ketones and Benzylamines

2012 ◽  
Vol 355 (1) ◽  
pp. 170-180 ◽  
Author(s):  
Huawen Huang ◽  
Xiaochen Ji ◽  
Wanqing Wu ◽  
Huanfeng Jiang
Keyword(s):  
Oxidative Cyclization ◽  
Aryl Ketones ◽  
Practical Synthesis

Heterogeneous Copper(I)-Catalyzed Cascade Addition–Oxidative Cyclization of Nitriles with 2-Aminopyridines or Amidines: Efficient and Practical Synthesis of 1,2,4-Triazoles

Synthesis ◽  
2019 ◽  
Vol 51 (09) ◽  
pp. 2014-2022 ◽  
Author(s):  
Jianhui Xia ◽  
Xue Huang ◽  
Mingzhong Cai
Keyword(s):  
Catalytic Activity ◽  
Oxidative Cyclization ◽  
Triazole Derivatives ◽  
Step Procedure ◽  
Practical Synthesis ◽  
High Yields ◽  
Mcm 41

The heterogeneous cascade addition-oxidative cyclization of nitriles with 2-aminopyridines or amidines was achieved in 1,2-dichlorobenzene or DMSO at 120–130 °C by using a 1,10-phenanthroline-functionalized MCM-41-supported copper(I) complex [Phen-MCM-41-CuBr] as the catalyst and air as the oxidant. The approach was used to generate a wide variety of 1,2,4-triazole derivatives in mostly high yields. This heterogeneous copper(I) catalyst could be easily prepared in a two-step procedure from commercially or readily available and inexpensive reagents and it exhibited higher catalytic activity than the CuBr/1,10-Phen system. Phen-MCM-41-CuBr was also easy to recover and was recyclable up to eight times with almost consistent activity.

ChemInform Abstract: Practical Synthesis of the Rebeccamycin Aglycone and Related Analogues by Oxidative Cyclization of Bisindolylmaleimides with a Wacker-Type Catalytic System.

ChemInform ◽  
2010 ◽  
Vol 33 (11) ◽  
pp. no-no
Author(s):  
Jianji Wang ◽  
Miguel Rosingana ◽  
Daniel J. Watson ◽  
Eric D. Dowdy ◽  
Robert P. Discordia ◽  
...  
Keyword(s):  
Catalytic System ◽  
Oxidative Cyclization ◽  
Practical Synthesis

Practical synthesis of the rebeccamycin aglycone and related analogs by oxidative cyclization of bisindolylmaleimides with a Wacker-type catalytic system

2001 ◽  
Vol 42 (51) ◽  
pp. 8935-8937 ◽  
Author(s):  
Jianji Wang ◽  
Miguel Rosingana ◽  
Daniel J Watson ◽  
Eric D Dowdy ◽  
Robert P Discordia ◽  
...  
Keyword(s):  
Catalytic System ◽  
Oxidative Cyclization ◽  
Practical Synthesis

Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone

2017 ◽  
Vol 68 (1) ◽  
pp. 180-185
Author(s):  
Adriana Maria Andreica ◽  
Lucia Gansca ◽  
Irina Ciotlaus ◽  
Ioan Oprean
Keyword(s):  
Sex Pheromone ◽  
Coupling Reaction ◽  
Coupling Scheme ◽  
Lithium Aluminium Hydride ◽  
Terminal Alkyne ◽  
Mercury Derivative ◽  
Lithium Aluminium ◽  
Convenient Synthesis ◽  
Practical Synthesis ◽  
Insect Sex

Were developed new and practical synthesis of (Z)-7-dodecene-1-yl acetate and (E)-9-dodecene-1-yl acetate. The routes involve, as the key step, the use of the mercury derivative of the terminal-alkyne w-functionalised as intermediate. The synthesis of (Z)-7-dodecene-1-yl acetate was based on a C6+C2=C8 and C8+C4=C12 coupling scheme, starting from 1,6-hexane-diol. The first coupling reaction took place between 1-tert-butoxy-6-bromo-hexane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-oct-7-yne, which is transformed in di[tert-butoxy-oct-7-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromobutane obtaining 1-tert-butoxy-dodec-7-yne. After acetylation and reduction with lithium aluminium hydride of 7-dodecyne-1-yl acetate gave (Z)-7-dodecene-1-yl acetate with 96 % purity. The synthesis of (E)-9-dodecene-1-yl acetate was based on a C8+C2=C10 and C10+C2=C12 coupling scheme, starting from 1,8-octane-diol. The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromoethane obtaining 1-tert-butoxy-dodec-9-yne. After reduction with lithium aluminium hydride of 1-tert-butoxy-(E)-9-dodecene and acetylation was obtained (E)-9-dodecene-1-yl acetate with 97 % purity.

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