Kabachnik–Fields reaction: Difference between revisions
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The '''Kabachnik–Fields reaction''' is an [[organic reaction]] forming an α-[[amino]] [[phosphonate]] from an [[amine]], a [[carbonyl]] compound and a dialkyl phosphonate. Aminophosphonates are synthetic targets of some importance as [[phosphorus]] analogues of α-[[amino acid]]s (a [[bioisosterism|bioisosteric]]). This [[multicomponent reaction]] was independently discovered by [[Martin Izrailevich Kabachnik]]<ref>{{cite journal| last=Kabachnik | first=Martin I. | |
The '''Kabachnik–Fields reaction''' is an [[organic reaction]] forming an α-[[amino]] [[phosphonate]] from an [[amine]], a [[carbonyl]] compound and a dialkyl phosphonate. Aminophosphonates are synthetic targets of some importance as [[phosphorus]] analogues of α-[[amino acid]]s (a [[bioisosterism|bioisosteric]]). This [[multicomponent reaction]] was independently discovered by [[Martin Izrailevich Kabachnik]]<ref>{{cite journal| last=Kabachnik | first=Martin I. |author2=T. Ya. Medved | year=1952 | title=Новый метод синтеза сс-аминофосфиновых кислот | trans_title=<!-- A new method for the synthesis of α-amino ? acids --> | journal=[[Doklady Akademii Nauk SSSR]] | volume=83 | page=689}}</ref> and [[Ellis K. Fields]]<ref>{{cite journal| last=Fields | first=Ellis K. | year=1952 | title=The synthesis of esters of substituted amino phosphonic acids | journal=[[Journal of the American Chemical Society]] | volume=74 | issue=6 | pages=1528–1531 | doi=10.1021/ja01126a054}}</ref> in 1952. |
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:[[Image:Kabachnik-Fields Reaction.svg|Kabachnik-Fields Reaction]] |
:[[Image:Kabachnik-Fields Reaction.svg|Kabachnik-Fields Reaction]] |
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The first step in this reaction is the formation of an [[imine]] followed by an [[addition reaction]] of the phosphonate P-H bond into the C=N double bond (a [[Abramov reaction|Pudovik reaction]]).<ref>{{cite journal| last=Zefirov | first=Nikolay S. | |
The first step in this reaction is the formation of an [[imine]] followed by an [[addition reaction]] of the phosphonate P-H bond into the C=N double bond (a [[Abramov reaction|Pudovik reaction]]).<ref>{{cite journal| last=Zefirov | first=Nikolay S. |author2=Elena D. Matveeva | date=2008-01-18 | title=Catalytic Kabachnik-Fields reaction: New horizons for old reaction | journal=[[ARKIVOC]] | volume=2008 | issue=i | pages=1–17 | url=http://www.arkat-usa.org/get-file/22930/?wikipedia-format=.pdf | accessdate=2009-12-08}}</ref> A related reaction is the [[Mannich reaction]]. |
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The reaction is accelerated with a combination of dehydrating reagent and [[Lewis acid]]. The carbonyl component in the reaction is usually an [[aldehyde]] and sometimes a [[ketone]]. |
The reaction is accelerated with a combination of dehydrating reagent and [[Lewis acid]]. The carbonyl component in the reaction is usually an [[aldehyde]] and sometimes a [[ketone]]. |
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Revision as of 13:44, 13 May 2014
The Kabachnik–Fields reaction is an organic reaction forming an α-amino phosphonate from an amine, a carbonyl compound and a dialkyl phosphonate. Aminophosphonates are synthetic targets of some importance as phosphorus analogues of α-amino acids (a bioisosteric). This multicomponent reaction was independently discovered by Martin Izrailevich Kabachnik[1] and Ellis K. Fields[2] in 1952.
The first step in this reaction is the formation of an imine followed by an addition reaction of the phosphonate P-H bond into the C=N double bond (a Pudovik reaction).[3] A related reaction is the Mannich reaction.
The reaction is accelerated with a combination of dehydrating reagent and Lewis acid. The carbonyl component in the reaction is usually an aldehyde and sometimes a ketone.
References
- ^ Kabachnik, Martin I.; T. Ya. Medved (1952). "Новый метод синтеза сс-аминофосфиновых кислот". Doklady Akademii Nauk SSSR. 83: 689.
{{cite journal}}: Cite has empty unknown parameter:|trans_title=(help) - ^ Fields, Ellis K. (1952). "The synthesis of esters of substituted amino phosphonic acids". Journal of the American Chemical Society. 74 (6): 1528–1531. doi:10.1021/ja01126a054.
- ^ Zefirov, Nikolay S.; Elena D. Matveeva (2008-01-18). "Catalytic Kabachnik-Fields reaction: New horizons for old reaction" (PDF). ARKIVOC. 2008 (i): 1–17. Retrieved 2009-12-08.