- 2-Bromo-2-chloro-3-arylpropanenitriles as C-3 Synthons for the Synthesis of Functionalized 3-Aminothiophenes
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2-Bromo-2-chloro-3-arylpropanenitriles can be prepared by Meerwein reaction from 2-chloroacrylonitrile and various aryldiazonium salts under copper(II) bromide catalysis. They proved to be stable compounds which form 2-chlorocinnnamonitriles upon treatment with bases. Reaction of the title compounds with substituted thioglycolates gave substituted 3-aminothiophenes which have not yet been accessible by other routes. Three-component reactions with the title compound, sodium sulfide and bromonitromethane, chloroacetonitrile, or ethyl 4-chloroacetoacetate gave 2-nitro- and 2-cyano-substituted 3-aminothiophenes, and thienopyridinediones in high yields and in one single step, respectively.
- Batsyts, Sviatoslav,Shehedyn, Maksym,Goreshnik, Evgeny A.,Obushak, Mykola D.,Schmidt, Andreas,Ostapiuk, Yurii V.
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p. 7842 - 7856
(2019/12/24)
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- Stereoselective Direct Chlorination of Alkenyl MIDA Boronates: Divergent Synthesis of E and Z α-Chloroalkenyl Boronates
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The individual molecules of α-chloroalkenyl boronates include both an electrophilic C?Cl bond and a nucleophilic C?B bond, which makes them intriguing organic synthons. Reported herein is a stereodivergent synthesis of both E and Z α-chloroalkenyl N-methyliminodiacetyl (MIDA) boronates through the direct chlorination of alkenyl MIDA boronates using tBuOCl and PhSeCl reagents, respectively. Both reaction processes are stereospecific and the use of sp3-B MIDA boronate is the key contributor to the reactivity. The synthetic value of the boronate products was also demonstrated.
- Zeng, Yao-Fu,Ji, Wei-Wei,Lv, Wen-Xin,Chen, Yunyun,Tan, Dong-Hang,Li, Qingjiang,Wang, Honggen
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p. 14707 - 14711
(2017/10/23)
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- Fe(0)-mediated synthesis of tri- and tetra-substituted olefins from carbonyls: An environmentally friendly alternative to Cr(II)
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Fe(0) was investigated as a cost-effective, environmentally friendly alternative to Cr(II) for the olefination of carbonyls by activated polyhalides. In many instances, Fe(0) was equivalent or superior to Cr(II). Notably, Fe(0), but not Cr(II), proved com
- Falck,Bejot, Romain,Barma, Deb K.,Bandyopadhyay, Anish,Joseph, Suju,Mioskowski, Charles
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p. 8178 - 8182
(2007/10/03)
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- Chemo- and stereoselectivity of the reaction of aromatic aldehydes with triphenylphosphine and trichloroacetic acid derivatives
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Aromatic aldehydes react with triphenylphosphine and ethyl trichloroacetate or trichloroacetonitrile to give the corresponding benzylidene dichlorides or α-chlorocinnamic acid derivatives. The chemo- and regioselectivity of these reactions depend on both the substituent in the aromatic ring and reaction conditions. The product configuration was determined on the basis of the coupling constants 2JCH and 3JCH in the 13C NMR spectra. Pleiades Publishing, Inc., 2006.
- Matveeva,Erin,Osetrov,Leshcheva,Kurts
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p. 388 - 392
(2007/10/03)
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