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			{{Distinguish|Pisatin|Anisatin|Amlodipine{{!}}Amlodipine (Istin)}}
	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 415666684
			| verifiedrevid = 443879827
	| ImageFile_Ref = {{chemboximage|correct|??}}		| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageFile = Instatin.png		| ImageFile1 = Isatine.svg
	| ImageSize =		| ImageSize1 =
			| ImageFile2 = IsatinPowder.jpg
	| IUPACName = 1''H''-indole-2,3-dione
			| ImageSize2 =
			| PIN = 1''H''-Indole-2,3-dione
	| OtherNames =		| OtherNames =
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
			| CASNo = 91-56-5
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| CASNo_Ref = {{cascite|correct|CAS}}
			| Beilstein = 383659
			| ChEBI_Ref = {{ebicite|correct|EBI}}
			| ChEBI = 27539
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 6787		| ChemSpiderID = 6787
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 326294		| ChEMBL = 326294
			| EC_number = 202-077-8
			| Gmelin = 165206
			| KEGG_Ref = {{keggcite|correct|kegg}}
			| KEGG = C11129
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 82X95S7M06
			| PubChem = 7054
			| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
			| DrugBank = DB02095
			| SMILES = O=C2c1ccccc1NC2=O
			| InChI=1/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)		| StdInChI = 1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = JXDYKVIHCLTXOP-UHFFFAOYSA-N		| StdInChIKey = JXDYKVIHCLTXOP-UHFFFAOYSA-N
	| CASNo = 91-56-5
	| CASNo_Ref = {{cascite|correct|CAS}}
	| PubChem =
	| DrugBank = DB02095
	| ChEBI = 27539
	| SMILES = O=C2c1ccccc1NC2=O
	| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C11129
	| InChI=1/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>8</sub>H<sub>5</sub>NO<sub>2</sub>		| Formula = C<sub>8</sub>H<sub>5</sub>NO<sub>2</sub>
	| MolarMass = 147.1308 g/mol		| MolarMass = 147.1308 g/mol
	| Appearance = Orange-red solid		| Appearance = Orange-red solid
	| Density =		| Density =
	| MeltingPtC = 200		| MeltingPtC = 200
	| BoilingPt =		| BoilingPt =
	| Solubility =		| Solubility =
	}}		}}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
			| MainHazards =
	| EUClass = Harmful ('''Xn''')
	| MainHazards =		| FlashPt =
	| FlashPt =		| AutoignitionPt =
			| GHSPictograms = {{GHS07}}
	| Autoignition =
			| GHSSignalWord = Warning
	| RPhrases = {{R22}} {{R36}} {{R37}} {{R38}}
			| HPhrases = {{H-phrases|302|315|319|335}}
			| PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+340|305+351+338|312|321|330|332+313|337+313|362|403+233|405|501}}
	}}		}}
	}}		}}
	'''Isatin''' or '''1''H''-indole-2,3-dione''' is an ] derivative. The compound was first obtained by Erdman<ref>{{cite journal
	| author= Otto Linné Erdmann
	| title = Untersuchungen über den Indigo
	| journal = ]
	| year = 1840
	| volume = 19
	| issue = 1
	| pages = 321–362
	| doi = 10.1002/prac.18400190161}}</ref> and ]<ref>{{cite journal
	| author= Auguste Laurent
	| title = Recherches sur l'indigo
	| journal = ]
	| year = 1840
	| volume = 3
	| issue = 3
	| pages = 393–434
	| url = http://gallica.bnf.fr/ark:/12148/bpt6k347443/f370.table}}</ref> in 1841 as a product from the ] of ] by ] and ]s. The compound is found in many plants.
			'''Isatin''', also known as '''tribulin''', is an ] derived from ] with formula C<sub>8</sub>H<sub>5</sub>NO<sub>2</sub>. The compound was first obtained by Otto Linné Erdman<ref>{{cite journal |last1=Erdmann |first1=Otto Linné |title=Untersuchungen über den Indigo |journal=Journal für Praktische Chemie |date=1840 |volume=19 |issue=1 |pages=321–362|doi=10.1002/prac.18400190161 |url=https://zenodo.org/record/1427782 }}</ref> and Auguste Laurent<ref>{{cite journal |last1=Laurent |first1=Auguste |title=Recherches sur l'indigo |journal=Annales de Chimie et de Physique |date=1840 |volume=3 |issue=3 |pages=393–434}}</ref> in 1840 as a product from the oxidation of ] by ] and ].<br>
	]s of isatin are investigated for their pharmaceutical properties .<ref>''Synthesis of 3,3´-bis-2H-indol-2-one as a novel bis-Schiff base'' A. A. Jarrahpour, D. Khalili ] '''2005''', M437 </ref>
			Isatin is a well-known natural product which can be found in plants of the genus '']'', in '']'',<ref>{{cite journal |last1=Pinto |first1=A. C. |journal=J. Braz. Chem. Soc.|title=The chemistry of isatins: a review from 1975 to 1999 |date=2001 |volume=12 |issue=3 |page=273|doi=10.1590/S0103-50532001000300002 |doi-access=free }}</ref><ref>{{cite journal |last1=Bergman |first1=J. |journal=Tetrahedron|title=The structure and properties of some indolic constituents in Couroupita guianensis aubl |date=1988 |volume=41 |issue=14 |page=2879|doi=10.1016/S0040-4020(01)96609-8 }}</ref> and also in humans, as a metabolic derivative of ].<ref>{{cite journal |last1=Chiyanzu |first1=I. |journal=Bioorg. Med. Chem. Lett. |title=Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain|date=2003 |volume=13 |issue=20 |pages=3527–30 |doi=10.1016/S0960-894X(03)00756-X |pmid=14505663 }}</ref> <br>
	Isatin forms a blue dye if it is mixed with ] and crude ]. The formation of the blue ] was long believed to be a reaction with benzene. ] was able to isolate the substance responsible for this reaction from benzene. This new heterocyclic compound was ].<ref>{{cite journal
	| author= Ward C. Sumpter
	| title = The Chemistry of Isatin
	| journal = ]
	| year = 1944
	| volume = 34
	| issue = 3
	| pages = 393–434
	| doi = 10.1021/cr60109a003}}</ref>
			It looks like a red-orange powder, and it is usually employed as building block for the synthesis of a wide variety of ] compounds including ],<ref>{{cite journal |last1=Mallamo |first1=J.P. |journal=Bioorg. Med. Chem. Lett.|title=Structure-guided identification of novel VEGFR-2 kinase inhibitors via solution phase parallel synthesis |date=2006 |volume=16 |issue=8 |pages=2158–62 |doi=10.1016/j.bmcl.2006.01.063 |pmid=16460933 }}</ref> ],<ref>{{cite journal |last1=He |first1=Y. |journal=Bioorg. Med. Chem. Lett.|title=Design, synthesis, and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors |date=2006 |volume=16 |issue=8 |pages=2109–12 |doi=10.1016/j.bmcl.2006.01.066 |pmid=16464578 }}</ref> anti-HIVs,<ref>{{cite journal |last1=Sriram |first1=D. |journal=Bioorg. Med. Chem. Lett.|title=Synthesis and evaluation of anti-HIV activity of isatin beta-thiosemicarbazone derivatives |date=2005 |volume=15 |issue=20 |pages=4451–5 |doi=10.1016/j.bmcl.2005.07.046 |pmid=16115762 }}</ref> and ].<ref>{{cite journal |last1=Bin-Jubair |first1=F.A.S.|title= Anti-Tubercular activity of Isatin and Derivatives |journal=Int. J. Res. Pharm. Sci. |date=2010 |volume=1 |page=113}}</ref> <br>
	==Preparation==
	Isatin is commercially available. It may be prepared from cyclicizing the condensation product of ], ] and ] in ]:.<ref>{{OrgSynth | title = Isatin | author = C. S. Marvel and G. S. Hiers | collvol = 1 | collvolpages = 327 | year = 1941 | prep = cv1p0327}}</ref><ref>]: ''Über Isonitrosoacetanilide und deren Kondensation zu Isatinen'', in: '']'' '''1919''', ''2&nbsp;(1)'', 234–242; {{DOI|10.1002/hlca.19190020125}}.</ref> This reaction is called the '''Sandmeyer isonitrosoacetanilide Isatin Synthesis''' and discovered by ] in 1919.
			The isatin core is also responsible for the color of “]” and “Maya yellow” dyes.<ref>{{cite journal |last1=Vuzquez de Agredos-Pascual |first1=M.L. |journal=Angew. Chem. Int. Ed.|title=From Maya Blue to "Maya Yellow": A Connection between Ancient Nanostructured Materials from the Voltammetry of Microparticles |date=2011 |volume=50 |issue=25 |pages=5741–4 |doi=10.1002/anie.201100921 |pmid=21557419 }}</ref>
	:]
	Another classic reaction, the Sandmeyer diphenylurea isatin synthesis (Sandmeyer 1903), starts from diphenylthiourea, ], and ] <ref></ref>
	Isatins can be made from the corresponding indole in good yield by a mix of ] and ] in a ]-] solution at 80°C.<ref>{{cite journal
			==Synthesis==
	| author= Yadav, J. S.
			===Sandmeyer methodology===
	| title = Indium(III) Chloride/2-Iodoxybenzoic Acid: A Novel Reagent System for the Conversion of Indoles to Isatins
			The Sandmeyer methodology is the oldest and straightforward way for the synthesis of isatin.<ref>{{cite journal |last1=Sandmeyer |first1=T. |title=Über Isonitrosoacetanilide und deren Kondensation zu Isatinen |journal=Helv. Chim. Acta |date=1919 |volume=2 |page=234|doi=10.1002/hlca.19190020125 |url=https://zenodo.org/record/1426793 }}</ref> The method involves the condensation between ] and a primary arylamine (e.g. ]), in the presence of ], in aqueous ] to form an α‐isonitrosoacetanilide. Isolation of this intermediate and subsequent ] promoted by strong acids (e.g. ]) furnishes isatin in >75% yield.
	| journal = ]
	| year = 2007
			]<br>
	| volume =2007
	| issue = 5
			===Stolle methodology===
	| pages = 693–696
			The Stolle procedure is considered the best alternative to Sandmeyer methodology for the synthesis of both substituted and unsubstituted isatins.<ref>{{cite journal |last1=Stollé |first1=R. |title=Über N-substituierte Oxindole und Isatine |journal=J. Prakt. Chem. (In German) |date=1922 |volume=105 |issue=1 |pages=137–148|doi=10.1002/prac.19221050111 |url=https://zenodo.org/record/1428064 }}</ref> In this case primary or secondary arylamines are condensed with ] to form a chlorooxalylanilide intermediate which can then cyclize in the presence of a ] (e.g. ], ], ], ''etc''.).
	| doi = 10.1055/s-2007-965930
	| last2= Reddy
			]<br>
	| first2= B.
	| last3= Reddy
			===Other procedures===
	| first3= Ch.
			More recent approaches to the synthesis of N-substituted isatins involves the direct ] of commercially available, substituted indoles or oxindoles with different ] such as ],<ref>{{cite journal |last1=Ji |first1=S.J. |journal=Org. Lett. |title=I2/TBHP-Catalyzed Chemoselective Amination of Indoles |date=2014 |volume=16 |pages=3094–3097}}</ref> ],<ref>{{cite journal |last1=Kirsch |first1=S.F. |journal=Synthesis|title=Synthesis of Isatins through Direct Oxidation of Indoles with IBX-SO3K/NaI |date=2015 |volume=47 |issue=13 |pages=1937–1943|doi=10.1055/s-0034-1380517 }}</ref> ]<ref>{{cite journal |last1=Wei |first1=W.T. |journal=Synlett|title=Synthesis of Indoline-2,3-diones by Radical Coupling of Indolin-2-ones with tert-Butyl Hydroperoxide |date=2018 |volume=29 |issue=2 |pages=215–218|doi=10.1055/s-0036-1589106 }}</ref> ''etc''.
	| last4= Krishna
	| first4= A.}}</ref>
			]<br>
			==Reactivity==
			The presence of an ], a ] and a ] moiety, gives to isatin the rare potential to be used as both an ] and a ]: indeed, it undergoes an enormous number of reactions, such as N-substitutions, ] at positions C-5 and C-7 of the phenyl ring, ] onto the C-3 ], ], ], ] and ]. Because of this unique reactivity, isatin is considered one of the most valuable ] in ].
			===''N''-Substitution===
			The ''N''-functionalization of the isatin core can be readily obtained by the ] of the amino moiety, forming the corresponding ] or ], and subsequent addition of an ] (e.g. alkyl or acyl ]).
			]
			On the other hand, ''N''-arylation is usually achieved by ] with ] using ] or ].<ref>{{cite journal |last1=Coppola |first1=Gary M. |title=Arylation of isatins. A direct route to -arylisatoic anhydrides |journal=Journal of Heterocyclic Chemistry |date=September 1987 |volume=24 |issue=5 |pages=1249–1251 |doi=10.1002/jhet.5570240503}}</ref><ref>{{cite journal |last1=Majumder |first1=Arpi |last2=Gupta |first2=Ragini |last3=Mandal |first3=Mrinmay |last4=Babu |first4=Madhu |last5=Chakraborty |first5=Debashis |title=Air-stable palladium(0) phosphine sulfide catalysts for Ullmann-type C–N and C–O coupling reactions |journal=Journal of Organometallic Chemistry |date=April 2015 |volume=781 |pages=23–34 |doi=10.1016/j.jorganchem.2014.11.018}}</ref>
			]
			===Ring expansion===
			In the field of ], ] are considered valuable reactions since they allow the obtainment medium-size ring (7-9 atoms) which are difficult to synthesize through "classical" methods.<ref>{{cite journal |last1=Donald |first1=James R. |last2=Unsworth |first2=William P. |title=Ring-Expansion Reactions in the Synthesis of Macrocycles and Medium-Sized Rings |journal=Chemistry - A European Journal |date=3 July 2017 |volume=23 |issue=37 |pages=8780–8799 |doi=10.1002/chem.201700467|pmid=28295709 |url=http://eprints.whiterose.ac.uk/114123/1/CEJ_SuRE_medium_ring_paper_accepted_article_manuscript.docx }}</ref><br>
			To date, only few articles concerning the ring expansion of isatin derivatives has been reported.
			The first one is an acid-catalyzed one-pot ] involving isatins, aminouracils, and isooxazolones to form isoxazoquinolines, important ] in ].<ref>{{cite journal |last1=Poomathi |first1=Nataraj |last2=Mayakrishnan |first2=Sivakalai |last3=Muralidharan |first3=Doraiswamy |last4=Srinivasan |first4=Rajagopal |last5=Perumal |first5=Paramasivan T. |title=Reaction of isatins with 6-amino uracils and isoxazoles: isatin ring-opening vs. annulations and regioselective synthesis of isoxazole fused quinoline scaffolds in water |journal=Green Chemistry |date=2015 |volume=17 |issue=6 |pages=3362–3372 |doi=10.1039/c5gc00006h}}</ref>
			]
			In another one-pot ], a unique two-carbon expansion has been achieved by reacting isatin with indene-1,3-dione and N-substituted ] to form dibenzoazepin-6-ones.<ref>{{cite journal |last1=Shi |first1=Rong-Guo |last2=Wang |first2=Xiao-Hua |last3=Liu |first3=Ruzhang |last4=Yan |first4=Chao-Guo |title=Two-carbon ring expansion of isatin: a convenient construction of a dibenzoazepinone scaffold |journal=Chemical Communications |date=2016 |volume=52 |issue=37 |pages=6280–6283 |doi=10.1039/c6cc00525j|pmid=27079548 |s2cid=36547699 }}</ref>
			]
			===''C-2''/''C-3'' nucleophilic addition===
			Isatin suffers ] on ] at ''C-2'' and ''C-3'' positions. The ] of the process strongly depends both on the ] (properties of the ] on the isatin core, especially those bonded to the nitrogen atom) and the reaction conditions (], temperature etc.). In some cases the ] could be followed by secondary reactions (''e.g.'' ], ], ] ''etc.'')
			[[File:Isatin nuclophilic addition.jpg|thumb|center|950px|Example of solvent-dependent nucleophlic addition to isatin<ref>{{cite journal |last1=Bergman |first1=Jan |last2=Stålhandske |first2=Claes |last3=Vallberg |first3=Hans |title=Studies of the Reaction between Indole-2,3-diones (Isatins) and Secondary Aliphatic Amines. |journal=Acta Chemica Scandinavica |date=1997 |volume=51 |pages=753–759 |doi=10.3891/acta.chem.scand.51-0753|url=http://actachemscand.org/pdf/acta_vol_51_p0753-0759.pdf |doi-access=free }}</ref>
			]]
			===Oxidation===
			The oxidation of isatin using ] (]) or ] yields ],<ref name=Mangold>{{cite journal |last1=Reissenweber |first1=Gernot |last2=Mangold |first2=Dietrich |title=Oxidation of Isatins to Isatoic Anhydrides and 2,3-Dioxo-1,4-benzoxazines |journal=Angewandte Chemie International Edition in English |date=March 1980 |volume=19 |issue=3 |pages=222–223 |doi=10.1002/anie.198002221}}</ref><ref>{{cite journal |last1=Yang |first1=Shuangshuang |last2=Li |first2=Xishuai |last3=Hu |first3=Fangfang |last4=Li |first4=Yinlong |last5=Yang |first5=Yunyun |last6=Yan |first6=Junkai |last7=Kuang |first7=Chunxiang |last8=Yang |first8=Qing |title=Discovery of Tryptanthrin Derivatives as Potent Inhibitors of Indoleamine 2,3-Dioxygenase with Therapeutic Activity in Lewis Lung Cancer (LLC) Tumor-Bearing Mice |journal=Journal of Medicinal Chemistry |date=25 October 2013 |volume=56 |issue=21 |pages=8321–8331 |doi=10.1021/jm401195n|pmid=24099220 }}</ref><ref>{{cite journal |last1=Bao |first1=Yajie |last2=Yan |first2=Yizhe |last3=Xu |first3=Kun |last4=Su |first4=Jihu |last5=Zha |first5=Zhenggen |last6=Wang |first6=Zhiyong |title=Copper-Catalyzed Radical Methylation/C–H Amination/Oxidation Cascade for the Synthesis of Quinazolinones |journal=The Journal of Organic Chemistry |date=20 April 2015 |volume=80 |issue=9 |pages=4736–4742 |doi=10.1021/acs.joc.5b00191|pmid=25849218 }}</ref> a compound widely used either in ] products and in ]. The use of ] gives rise to ] compounds.<ref name=Mangold />
			]
			===Dimerization===
			Dimerization of isatin with ] in methanol yield ].<ref>{{cite journal |last1=Wang |first1=Cuiling |last2=Yan |first2=Jiaxu |last3=Du |first3=Mo |last4=Burlison |first4=Joseph A. |last5=Li |first5=Chi |last6=Sun |first6=Yanni |last7=Zhao |first7=Danqing |last8=Liu |first8=Jianli |title=One step synthesis of indirubins by reductive coupling of isatins with KBH 4 |journal=Tetrahedron |date=May 2017 |volume=73 |issue=19 |pages=2780–2785 |doi=10.1016/j.tet.2017.03.077}}</ref> This represent the ]'s red component and a highly effective ] compound.
			]
			===Reduction===
			Reduction of the non-amide carbonyl group obviously occurs to give ], respectively.
			==See also==
			* ]
	== References ==		== References ==
			{{reflist}}
	<references/>
	==Further reading==		==Reviews==
			*{{cite book|doi=10.1016/S0065-2725(08)60127-0|volume=18|pages=1–58|year=1975|last1=Popp|first1=Prank D.|title=Advances in Heterocyclic Chemistry Volume 18 |chapter=The Chemistry of Isatin |isbn=9780120206186}}
	* {{cite journal | author = Piyasena Hewawasam and Nicholas A. Meanwell | title = A general method for the synthesis of isatins | journal = ] | volume = 35 | issue = 40 | pages = 7303–6 | year = 1994 | doi = 10.1016/0040-4039(94)85299-5}}
			*{{cite journal |last1=Silva |first1=Joaquim F. M. da |last2=Garden |first2=Simon J. |last3=Pinto |first3=Angelo C. |title=The chemistry of isatins: a review from 1975 to 1999 |journal=Journal of the Brazilian Chemical Society |date=June 2001 |volume=12 |issue=3 |pages=273–324 |doi=10.1590/S0103-50532001000300002|doi-access=free }}
	]
			*{{cite journal|doi=10.1134/S1070428009110013|title=New isatin derivatives|journal=Russian Journal of Organic Chemistry|volume=45|issue=11|pages=1583|year=2009|last1=Mesropyan|first1=E. G.|last2=Avetisyan|first2=A. A.|s2cid=97341279}}
	]
	]
			*{{cite journal |last1=Varun |first1=Varun |last2=Sonam |first2=Sonam |last3=Kakkar |first3=Rita |title=Isatin and its derivatives: a survey of recent syntheses, reactions, and applications |journal=MedChemComm |date=2019 |volume=10 |issue=3 |pages=351–368 |doi=10.1039/C8MD00585K|pmid=30996856 |pmc=6438150 }}
	]
	]
			==External links==
	]
			*{{cite EB1911 |wstitle=Isatin |volume=14 |pages=865–866 |short=1}}
	]
			]
			]