Reaction Outcome Critically Dependent on the Method of Workup: An Example from the Synthesis of 1-Isoquinolones
- Petr Matouš*Petr Matouš*Email: [email protected]Department of Bioorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05 Hradec Králové, Czech RepublicMore by Petr Matouš
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- Michal MájekMichal MájekDepartment of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Ilkovičova 6, Mlynská dolina, 842 15 Bratislava 4, SlovakiaMore by Michal Májek
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- Ondřej KysilkaOndřej KysilkaTrelleborg Bohemia, Akademika Bedrny 531/8a, Věkoše, 500 03 Hradec Králové Czech RepublicMore by Ondřej Kysilka
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- Jiří KunešJiří KunešDepartment of Bioorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05 Hradec Králové, Czech RepublicMore by Jiří Kuneš
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- Jana MaříkováJana MaříkováDepartment of Bioorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05 Hradec Králové, Czech RepublicMore by Jana Maříková
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- Aleš RůžičkaAleš RůžičkaDepartment of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 95, 532 10 Pardubice 2, Czech RepublicMore by Aleš Růžička
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- Milan Pour*Milan Pour*Email: [email protected]Department of Bioorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05 Hradec Králové, Czech RepublicMore by Milan Pour
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- Pavel Kočovský*Pavel Kočovský*Email: [email protected]Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43 Prague 2, Czech RepublicDepartment of Bioorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 500 05 Hradec Králové, Czech RepublicInstitute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo 2, 166 10 Prague 6, Czech RepublicMore by Pavel Kočovský
Abstract
A striking dependence on the method of workup has been found for annulation of benzonitriles ArC≡N to N-methyl 2-toluamide (1), facilitated by n-BuLi (2 equiv): quenching the reaction by a slow addition of water produced the expected 1-isoquinolones 2; by contrast, slow pouring of the reaction mixture into water afforded the cyclic aminals 5 (retaining the NMe group of the original toluamide). The mechanism of the two processes is discussed in terms of the actual H+ concentration in the workup. Both 2 and 5 were then converted into the corresponding 1-chloroisoquinolines 3, coupling of which, mediated by (Ph3P)2NiCl2/Zn, afforded bis-isoquinolines 4.
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