Bischler–Möhlau Indole Synthesis
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Bischler–Möhlau Indole Synthesis
The Bischler–Möhlau indole synthesis, also often referred to as "The Bischler Indole Synthesis," is a chemical reaction that forms a 2-aryl- indole from an α-bromo- acetophenone and excess aniline; it is named after August Bischler and . Despite its long history, this classical reaction had received relatively little attention in comparison with other methods for indole synthesis, owing to the reactions harsh conditions, poor yields and unpredictable regioselectivity. Recently, milder methods have been developed, including the use of lithium bromide as a catalyst and an improved procedure involving the use of microwave irradiation. History What is now known as the Bischler-Möhlau Indole Synthesis was discovered and formulated through the separate, but complimentary, findings of German Scientist Richard Möhlau in 1882 and Russia-born German chemist August Bischler (with partneH. Brion in 1892. These two researchers did not collaborate with each other, but instead indepe ...
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August Bischler
August Bischler (29 April 1865 – 26 May 1957) was a Russian Empire-born ethnic Crimea German chemist who later emigrated to Switzerland. He discovered the Bischler–Möhlau indole synthesis reaction in 1892 and, together with Bernard Napieralski, discovered the Bischler–Napieralski reaction in 1893. Life He received his Ph.D. at the University of Zurich 1889 worked at the University of Zurich and from 1899 at the University of Basel. After becoming a Swiss citizen in 1925 he worked in the chemical industry in Geneva. Bernard Napieralski Bernard Napieralski was a Ph.D. student of Bischler at the University of Zurich in 1893. Napieralski was born in Ostrowy, Poland Poland, officially the Republic of Poland, is a country in Central Europe. It is divided into 16 administrative provinces called voivodeships, covering an area of . Poland has a population of over 38 million and is the fifth-most populou ..., 1861. References * 1865 births 1957 deaths Che ...
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Synlett
''Synlett'' is an international scientific journal for accounts and rapid communications of original contributions of fundamental research in synthetic organic chemistry. The impact factor of this journal is 2.419 (2017). ''Nature'' featured a brief piece by the editor-in-chief of the journal in 2017, Benjamin List Benjamin ( he, ''Bīnyāmīn''; "Son of (the) right") blue letter bible: https://www.blueletterbible.org/lexicon/h3225/kjv/wlc/0-1/ H3225 - yāmîn - Strong's Hebrew Lexicon (kjv) was the last of the two sons of Jacob and Rachel (Jacob's thir ..., where he discussed the journal's experience with the non-traditional peer review system. References Chemistry journals Thieme academic journals Publications established in 1989 {{chem-journal-stub ...
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Bischler–Napieralski Reaction
The Bischler–Napieralski reaction is an intramolecular electrophilic aromatic substitution reaction that allows for the cyclization of β-arylethylamides or β-arylethylcarbamates. It was first discovered in 1893 by August Bischler and , in affiliation with Basle Chemical Works and the University of Zurich. The reaction is most notably used in the synthesis of dihydroisoquinolines, which can be subsequently oxidized to isoquinolines. Mechanisms Two types of mechanisms have appeared in the literature for the Bischler–Napieralski reaction. Mechanism I involves a dichlorophosphoryl imine-ester intermediate, while Mechanism II involves a nitrilium ion intermediate (both shown in brackets). This mechanistic variance stems from the ambiguity over the timing for the elimination of the carbonyl oxygen in the starting amide. In Mechanism I, the elimination occurs with imine formation ''after'' cyclization; while in Mechanism II, the elimination yields the nitrilium intermediate ''pri ...
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Fischer Indole Synthesis
The Fischer indole synthesis is a chemical reaction that produces the aromatic heterocycle indole from a (substituted) phenylhydrazine and an aldehyde or ketone under acidic conditions. The reaction was discovered in 1883 by Emil Fischer. Today antimigraine drugs of the triptan class are often synthesized by this method. This reaction can be catalyzed by Brønsted acids such as HCl, H2SO4, polyphosphoric acid and p-toluenesulfonic acid or Lewis acids such as boron trifluoride, zinc chloride, iron chloride, and aluminium chloride. Several reviews have been published. Reaction mechanism The reaction of a (substituted) phenylhydrazine with a carbonyl (aldehyde or ketone) initially forms a phenylhydrazone which isomerizes to the respective enamine (or 'ene-hydrazine'). After protonation, a cyclic ,3sigmatropic rearrangement occurs producing an imine. The resulting imine forms a cyclic aminoacetal (or ''aminal''), which under acid catalysis eliminates NH3, resulting in the ...
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Francis Robert Japp
Francis Robert Japp FRS (8 February 1848 – 1 August 1925) was a British chemist who discovered the Japp-Klingemann reaction in 1887. He was born in Dundee, Scotland, the son of James Japp, a minister of the Catholic Apostolic Church. He graduated from St Andrews with an M.A. in 1868 and entered the University of Edinburgh as a student of law. He left the university because of health problems and stayed in Germany for two years from 1871 until 1873. After returning to England he decided to study chemistry. He started his studies at the University of Heidelberg with Robert Bunsen, where he received his PhD in 1875. He joined the laboratory of August Kekulé at the University of Bonn the following year and after returning to Scotland in 1878 worked with Alexander Crum Brown at the University of Edinburgh. In 1881 Japp became assistant professor at the Royal School of Mines and Normal School of Science South Kensington and in 1890 Professor of Chemistry at the University of Aberd ...
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Bửu Hội
Prince Nguyễn Phúc Bửu Hội (c. 1915 – 28 January 1972) was a Vietnamese diplomat, scientist and cancer researcher. Family Born circa 1915, Bửu Hội was a native of the former imperial capital of Huế.Arcos, p. 2856B. He was a great-great-grandson of Emperor Minh Mạng, who ruled Vietnam from 1820 until his death in 1841. Mạng had been a staunch Confucianist, known for his conservative philosophy, in which he shunned the western world and technological and scientific innovations. He resisted Catholic and Buddhist missionaries in Vietnam and was known for his hostility toward them, as he believed they were undermining the Emperor's Mandate of Heaven. Mạng's father was Emperor Gia Long, who had united Vietnam under its current state. Gia Long had reunited the nation under the newly formed Nguyễn Dynasty with the help of French volunteers recruited by the Jesuit missionary Pigneau de Behaine after more than 200 years of north-south division and multiple wars ...
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Möhlau Indole Equation
Möhlau is a village and a former municipality in Wittenberg district in Saxony-Anhalt, Germany. Since 1 January 2011, it is part of the town Gräfenhainichen. It was part of the administrative community (''Verwaltungsgemeinschaft'') of Tor zur Dübener Heide. Geography The community lies on the southern edge of Wittenberg district about 9 km west of the former district seat of Gräfenhainichen and about 18 km southeast of Dessau, right on the border with Saxony. Geology The municipal area is strongly marked by brown coal strip mining. Most of the old pits have flooded since they were shut down and are now used as bathing ponds. Subdivisions Möhlau consists of the subdivisions of Golpa, Rothehaus, Großmöhlau, and Kleinmöhlau. History Möhlau is said to have been settled originally by Slavs. It had its first documentary mention on 12 December 1200 when a church was consecrated in Wörlitz is a town and a former municipality in the district of Wittenber ...
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Tetrahedron (journal)
''Tetrahedron'' is a weekly peer-reviewed scientific journal covering the field of organic chemistry. According to the ''Journal Citation Reports'', ''Tetrahedron'' has a 2020 impact factor of 2.457. ''Tetrahedron'' and Elsevier, its publisher, support an annual symposium. In 2010, complaints were raised over its high subscription cost. Notable papers , the Web of Science lists ten papers from ''Tetrahedron'' that have more than 1000 citations. The four articles that have been cited more than 2000 times are: * – cited 2228 times * – cited 2162 times * – cited 2124 times * – cited 2107 times See also * ''Tetrahedron Letters'' * ''Tetrahedron Computer Methodology'' * ''Polyhedron In geometry, a polyhedron (plural polyhedra or polyhedrons; ) is a three-dimensional shape with flat polygonal faces, straight edges and sharp corners or vertices. A convex polyhedron is the convex hull of finitely many points, not all on th ...'' (journal) Refere ...
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Richard Möhlau
Richard is a male given name. It originates, via Old French, from Old Frankish and is a compound of the words descending from Proto-Germanic ''*rīk-'' 'ruler, leader, king' and ''*hardu-'' 'strong, brave, hardy', and it therefore means 'strong in rule'. Nicknames include "Richie", "Dick", "Dickon", " Dickie", " Rich", " Rick", " Rico", "Ricky", and more. Richard is a common English, German and French male name. It's also used in many more languages, particularly Germanic, such as Norwegian, Danish, Swedish, Icelandic, and Dutch, as well as other languages including Irish, Scottish, Welsh and Finnish. Richard is cognate with variants of the name in other European languages, such as the Swedish "Rickard", the Catalan "Ricard" and the Italian "Riccardo", among others (see comprehensive variant list below). People named Richard Multiple people with the same name * Richard Andersen (other) * Richard Anderson (other) * Richard Cartwright (other) ...
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Regioselectivity
In chemistry, regioselectivity is the preference of chemical bonding or breaking in one direction over all other possible directions. It can often apply to which of many possible positions a reagent will affect, such as which proton a strong base will abstract from an organic molecule, or where on a substituted benzene ring a further substituent will be added. A specific example is a halohydrin formation reaction with 2-propenylbenzene: : Because of the preference for the formation of one product over another, the reaction is selective. This reaction is regioselective because it selectively generates one constitutional isomer rather than the other. Various examples of regioselectivity have been formulated as rules for certain classes of compounds under certain conditions, many of which are named. Among the first introduced to chemistry students are Markovnikov's rule for the addition of protic acids to alkenes, and the Fürst-Plattner rule for the addition of nucleophiles to ...
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