
	Where results make sense

Topic: Fischer indole synthesis

Related Topics

List of reactions

Indole

Electrophilic aromatic substitution

Pyrrole

Molecular mass

Indigo dye

Pacoima, California

	Indole - Wikipedia, the free encyclopedia (Site not responding. Last check: 2007-10-13)
		In the 1930s, interest in indole intensified when it became known that the indole nucleus is present in many important alkaloids, as well is in tryptophan and auxins, and it remains an active area of research today.
		Although the synthesis of indole itself is problematic using the Fischer indole synthesis, it is often used to generate indoles substituted in the 2- and/or 3-positions.
		In this case, the 2-aminofuran is the diene, whereas the indole is the dienophile.
	zomig.legalview.com /wikipedia/Indole (1153 words)

	Hermann Emil Fischer Summary
		Fischer's first step in unraveling the mysteries of the sugar group was the discovery in 1875 of phenyl hydrazine, a compound which could be used as a general reagent for separating and isolating sugars.
		Fischer was elected to membership in the Academy of Sciences, and, in 1902, he received the Nobel Prize "for his synthesis in the groups of sugars and purine," as quoted by Eduard Farber in Nobel Prize Winners in Chemistry.
		Fischer was born in Euskirchen, near Cologne, the son of a businessman.
	www.bookrags.com /Hermann_Emil_Fischer (4302 words)

	Fischer indole synthesis - Wikipedia, the free encyclopedia
		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 Hermann Emil Fischer.
		Using palladium chemistry developed at MIT by Stephen Buchwald, the Fischer indole synthesis can be completed using aryl bromides as starting materials.
	en.wikipedia.org /wiki/Fischer_indole_synthesis (240 words)

	Indole synthesis
		The synthesis of indoles alkaloids has been achieved employing a Bartoli synthesis/heteroaryl radical approach.
		A new, mild, and efficient method for the synthesis of polyfunctionalized indoles by direct reaction of substituted 2-chloroanilines with cyclic or acyclic ketones was developed.
		The synthesis of a series of indole and carbazole derivatives from 2-fluorophenyl imines is reported.
	www.organic-chemistry.org /synthesis/heterocycles/indoles.shtm (470 words)

	Hermann Emil Fischer - Wikipedia, the free encyclopedia
		Emil Fischer was born in Euskirchen, near Cologne, the son of a businessman.
		Even before 1880 the aldehyde formula of glucose had been indicated, but Fischer established it by a series of transformations such as oxidation into aldonic acid and the action of phenylhydrazine which he had discovered and which made possible the formation of the phenylhydrazones and the osazones.
		Fischer was made a Prussian Geheimrat (Excellenz), and held honorary doctorates of the Universities of Christiania, Cambridge (England), Manchester and Brussels.
	en.wikipedia.org /wiki/Hermann_Emil_Fischer (1209 words)

	The Fischer Indole Synthesis: A Semiempirical Study.
		Fischer indole synthesis is a well established procedure for the synthesis of substituted indoles.
		Several members of the indole alkaloid familiy, flavopereirin and sempervirin among them, have shown antitumor activity.[1] Since our drug-development efforts focus on the indoloquinolizinium moiety, recently we have become interested in synthesizing substituted tryptamines as intermediates for the synthesis of indoloquinolizinium analogues with enhanced antitumor activity.
		So it may well be that, in the resulting indole structures, the lone pair on the nitrogen fails to extend the aromatic system to the five-membered ring, and ring strain produces the increased energy.
	www.ch.ic.ac.uk /ectoc/echet98/pub/051/index.htm (1252 words)

	Heterocyclic Chemistry
		Indole is probably the most important fused ring heterocycle in this class.
		Finally, the Fischer indole synthesis is a remarkable sequence of tautomerism, sigmatropic rearrangement, nucleophilic addition, and elimination reactions occuring subsequent to phenylhydrazone formation.
		Whether the indole nitrogen is substituted or not, the favored site of attack is C-3 of the heterocyclic ring.
	www.cem.msu.edu /~reusch/VirtualText/heterocy.htm (4072 words)

	Behaviour of 1,3-disubstituted- 4,5,6,7-tetrahydrobenzo[c]thiophen-4-ones in the Fischer indole synthesis
		Among all the possibilities, the simplest method to obtain compouds 1 appeared to be using a Fischer indole synthesis on 1,3-disubstituted-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one derivatives 2, readilly accessible by known methods
		The Fischer indole synthesis, as a one-step procedure, applied to the thiophene 2a in refluxing acetic acid with phenylhydrazine hydrochloride did not lead to the expected thieno[a]carbazole 4 described by Buu-Hoï
		A mixture of substituted phenylhydrazine hydrochloride (4.6 mol) and the ketone (4.2 mol) in 50 ml of CH OH/HCl (100:1 v/v) was heated at 70 celsius for 24 h.
	www.ch.ic.ac.uk /ectoc/echet96/papers/010 (603 words)

	Future Synthetic Drugs of Abuse
		A modest literature search will convince a clandestine chemist that the use of the Fischer indole synthesis affords access to a greater variety of indole derivatives (Huisgen and Lux 1960; Robinson 1983) as it will also reduce the chance that law enforcement will be alerted by his purchases of essential chemicals.
		Relative to those which lack an aryl ring substitution, there is no doubt that the activity of psilocybin/psilocin upon ingestion is due to an enhancement of gastrointestinal absorption which, in turn, must be structurally related to the presence of the C-4 hydroxyl substitution.
		Then substitution of the indole nitrogen with either methyl or acetyl brings the total number of possible CsA's that can be argumentatively related to serotonin to 225.
	deoxy.org /deatarot.htm (1255 words)

	Metal-catalyzed arylations of hydrazines, hydrazones, and related substrates - Patent 6235936
		Additionally, the invention provides a conceptually novel strategy, the cornerstone of which is the transition metal-catalyzed arylation or vinylation method, for the synthesis of indoles, carbazoles, and the like.
		The ability to provide a synthesis scheme for hydrazines and the like which can be carried out under mild conditions and/or with non-polar solvents has broad application, especially in the agricultural and pharmaceutical industries, as well as in the polymer industry.
		The Fischer indole synthesis step in this embodiment is highly selective; the more electron-rich aryl moiety of the intermediate N,N-diaryl hydrazone is selectively incorporated into the indole nucleus of the product, and the less electron-rich aryl moiety appears as a substituent at the 1-position of the indole product.
	www.freepatentsonline.com /6235936.html (11745 words)

	Name Reactions in Heterocyclic Chemistry, Jie Jack Li (Editor) - ISBN 0471302155 - ELX.com.au (Australia)
		Because of the enormous amount and variety of information, it is often a difficult topic to cover for undergraduate and graduate chemistry students, even in simplified form.
		Yet the chemistry of heterocyclic compounds and methods for their synthesis form the bedrock of modern medicinal chemical and pharmaceutical research.
		Thus there is a great need for high quality, up-to-date, and authoritative books on heterocyclic synthesis helpful to both the professional research chemist as well as the advanced student.
	www.elx.com.au /item/0471302155 (282 words)

	Heteroaromatics - Chemistry (Site not responding. Last check: 2007-10-13)
		Non basic; as for pyrrole, the N lone pair is involved in aromatic system protonation occurs at C3 (as for enamine)
		Synthesis of Indole (Fischer indole synthesis)Fischer indole synthesis
		Diazoles could be considered as related to pyrrole but with a N replacing a CH group.
	chemistry.tidalswan.com /index.php?title=Heteroaromatics (656 words)

	About Us
		About Us Synectic Corporation was established in 1988 to focus on custom synthesis of small-volume organic chemicals, mostly for the pharmaceutical industry.
		Synectic has considerable expertise in the synthesis of Organoselenium compounds and in the synthesis of heterocycles, such as Thiazole and substituted Thiazoles, substituted Indoles and derivatives, substituted Imidazoles, Benzimidazoles, and Imidazolines, substituted Thiobarbituric acids, Isatins, Oxindoles Indazoles, Quinolines, Pyrimidines and Selenophenes.
		Synectic is also working in the areas of Carbohydrates and Oligosacharides, Amino Acids (racemic and chiral), and chiral compounds by both asymmetric synthesis and by resolution.
	www.synectic-corp.com /aboutus.htm (146 words)

	Microwave assisted synthesis of room temperature ionic liquid precursors
		Our aim was to reduce overall time of preparation of the ionic liquids and to synthesize the precursor salts on a large-scale in shorter time period.
		The use of a closed vessel allows for stoichiometric amounts of alkyl halides to be reacted, instead of excess, with no apparent loss of yield, highlights the ‘green’ aspect of this improved procedure.
		Khadilkar BM and Rebeiro GL, Chloroaluminate Ionic Iiquid for Fischer Indole Synthesis.
	www.mdpi.net /ecsoc-5/e0020/e0020.htm (1379 words)

	PEPPSI(TM) Catalysts
		Notably the terminal alkynyl TMS group in compound 7 is completely stable to the cross-coupling of an alkyl chloride under room temperature reaction conditions.
		Note that in the former case, a wide range of heteroatom-containing reaction partners were coupled in excellent yield.
		Notably, the synthesis of the naphthylol derivative shown in Figure 9 was successfully achieved on a 10 g scale in 85% yield, further cementing the industrial viability of this system.
	www.sigmaaldrich.com /Area_of_Interest/Chemistry/Chemical_Synthesis/Product_Highlights/PEPPSI.html (1307 words)

	Amazon.com: "Fischer Esterification": Key Phrase page (Site not responding. Last check: 2007-10-13)
		Strategic Applications of Named Reactions in Organic Synthesis by Laszlo Kurti, Barbara Czako
		The resulting carboxylate salt was converted to the methyl ester using Fischer esterification conditions under which the silyl protecting group was also removed.
		Fischer esterification B. E 1 elimination C. Saponification D. E2 elimination 207.
	www.amazon.com /phrase/Fischer-Esterification (503 words)

	Emil Hermann Fischer Information Center - Emil Hermann Fischer
		Emil Hermann Fischer Information Center - Emil Hermann Fischer
		Fischer was born in Euskirchen, near Cologne, Emil Hermann Fischer the son of a businessman.
		Back to the top of Emil Hermann Fischer.
	www.scipeeps.com /Sci-Chemistry_Topics_E_-_F/Emil_Hermann_Fischer.html (246 words)

	Lilienthal's Pharmacological & Chemical References
		formylation of indole with hexamethylenetetramine / AcOH, yield 25%
		synthesis of 4-MeO-indole, reaction with 1-dimethylamino-2-nitroethylene, LAH reduction to tryptamines
		psilocin and psilocybin extraction, UV and IR spectra, colour reactions, synthesis
	www.fortunecity.com /westwood/storey/116/referenc.htm (2338 words)

	2-Phenyl-indole derivatives - Patent 4113736
		By the same method but using the appropriate starting-products, the following compounds were prepared:
		______________________________________ 2-(4'-dodecyloxy-phenyl)-6-methyl- 206 (acetone) indole 2-(4'-methoxy-phenyl)-6-hydroxy-indole 252 (toluene-acetone 50/50) 2-(3'-methoxy-4'-hydroxy-phenyl)-5- 196 (benzene) methyl-indole 2-(4'-methoxy-phenyl)-6-methoxy-indole 230 (benzene-acetone 50/50) 2-(3'-methyl-4'-methoxy-phenyl)-7- 135 (benzene) methyl-indole 2-phenyl-6-methoxy-indole 177 (ethanol) 2-phenyl-5-methoxy-indole 166 (benzene- cyclohexane 7/3) ______________________________________
		______________________________________ 2-phenyl-6-hydroxy-indole 235 (ethanol-water 8/2) 2-(4'-hydroxy-phenyl)-5-hydroxy- 280 (toluene-acetone 50/50) indole ______________________________________
	www.freepatentsonline.com /4113736.html (2643 words)

	A Palladium-Catalyzed Strategy for the Preparation of Indoles: A Novel Entry into the Fischer Indole Synthesis
		A Palladium-Catalyzed Strategy for the Preparation of Indoles: A Novel Entry into the Fischer Indole Synthesis
		This starting material is suitable for fischer indole synthesis after hydrolysis and trapping of the liberated hydrazine with an excess of aldehyde or ketone.
		Die hierbei neu entstehenden Hydrazone reagieren nach Fischer zum Indol ab.
	www.organic-chemistry.org /abstracts/literature/490.shtm (141 words)

	Amazon.ca: The Fischer Indole Synthesis: Books: Brian Robinson (Site not responding. Last check: 2007-10-13)
		Amazon.ca: The Fischer Indole Synthesis: Books: Brian Robinson
		Publisher: learn how customers can search inside this book.
		Subjects > Science > Chemistry > Organic > Synthesis
	www.amazon.ca /Fischer-Indole-Synthesis-Brian-Robinson/dp/0471100099 (113 words)

	Buchwald Group - 1997-1998 Research Publications
		Wagaw, S.; Yang, B.H.; Buchwald, S.L. "A Palladium-Catalyzed Strategy for the Preparation of Indoles: A Novel Entry into the Fischer Indole Synthesis."
		Sadighi, J.P.; Singer, R.A.; Buchwald, S.L. "Palladium-Catalyzed Synthesis of Monodisperse, Controlled-Length and Functionalized Oligoanilines."
		Aoki, K.; Peat, A.J.; Buchwald, S.L. "A Titanocene-Based Method for Indole Synthesis."
	web.mit.edu /chemistry/buchwald/research/pubs/pubs1998-1997.html (478 words)

	Problem Set #1
		N=C=O, how could one demonstrate that the cyclic compound shown below is not an intermediate in the reaction?
		In the Fischer indole synthesis, an example of which is shown below, a phenylhydrazone is converted to an indole by the action of acid.
		Outline two experiments, one using isotopic labeling, the other without, to determine which of the two nitrogen atoms of the phenylhydrazone is incorporated in the indole.
	clem.mscd.edu /~wiederm/advorgchem/401problemset1.htm (630 words)

	Reactions (Site not responding. Last check: 2007-10-13)
		NORCHIM realizes multi steps synthesis involving the following chemical reactions
		ALKYLATION (O, N and C) CATALYTIC HYDROGENATION (up to 20 bars)
		METHYLATION (with (CH and most especially synthesis of various substituted heterocyclic rings.
	www.norchim.com /Reactions.htm (33 words)

Try your search on: Qwika (all wikis)