Phosphonic acids amino-, esters

CN [l-[[[(2-chloroethyl)nitrosoamino]carbonyl]amino]ethyl]phosphonic acid diethyl ester... 

Lukszo, J. and Tyka, R., New protective groups in the synthesis of 1-amino-alkane-phosphonic acids and esters. Synthesis, 2.19, 1977. 

Phosphonic acid amide esters. A soln. of ethyl [l-[[(phenylmethoxy)carbonyl]amino]-2-methylpropyl]phosphinate in acetonitrile under argon treated with bis(trimethyl-silyl)acetamide, followed after 1 min by L-alanine hydrochloride methyl ester, CCI4, and Et3N, the soln. stirred at room temp, for 30 min, cooled to 0°, and quenched with methanol N-[ethoxy[ 1 -[[(phenylmethoxy)carbonyl]am no]-2-methylpropyl]-... 

Jayashree, P., Shanthi, G., and Pemmal, P. T. (2009). Indium trichloride catalyzed one-pot synthesis of new (2-amino-3-cyano-4//-chromen-4-yl) phosphonic acid diethyl ester. Synlett, 917-920. 

Keywords Salicylaldehydes, malononitrile/ethyl cyanoacetate, triethylphosphite, nanocrystalline MgO heterogeneous catalyst, ethanol-water (1 1), room temperature, one-pot three-component synthesis, (2-amino-3-cyano-4//-chromen-4-yl)phosphonic acid diethyl esters... 

New diamine containing phosphonic acid groups - (4-[4,5-bis(3-amino-phenyl)-lH-imidazol-2-yl]-phenyl)phosphonic acid diethyl ester - [53] was... 

In 2011, Pore and his group reported a room temperature method for the rapid and efficient synthesis of (2-amino-3-cyano-4//-chromen-4-yl) phosphonic acid diethyl esters (34) via a single-step multi-component reaction of structurally diverse salicylaldehydes (32) with malononitrile (33) and triethyl phosphite, using a catalytic amount of potassium phosphate, in ethanol (Scheme 14). Use of potassium phosphate as an inexpensive catalyst, mild reaction conditions, and a simple work-up procedure are the added advantages of the present method. 

In the following year (2012), Rao Kolia and Lee extended the reaction for the synthesis of such biologically relevant 2-amino-4//-chromen-4-ylphosphonate derivatives (35) from the one-pot three-component condensation of substituted salicylaldehydes, malononitrile (or ethylcyanoacetate) and triethylphosphite in the presence of ethyle-nediamine diacetate (EDDA) as a catalyst in alcohol under room temperature conditions (Scheme 15). Recently, Brahmachari and Laskar (2014) have also developed an energy-efficient multicomponent one-pot procedure for the facile synthesis of a wide range of diverse (2-amino-3-cyano-4/f-chromen-4-yl)phosphonic acid diethyl esters at room temperature from the reaction of salicylaldehydes, malononitrile (or ethyl cyanoacetate) and triethylphosphite on the surface of a reusable heterogeneous MgO-nanocatalyst in aqueous ethanolic... 

Scheme 17 Proposed mechanism for the synthesis of 2-amino-3-cyano-4H-chromen-4-yi)phosphonic acid diethyi esters cataiyzed by nano-MgO.

Amino-3-cyano-4H-chromen-4-yl) phosphonic acid diethyl ester 35... 

Scheme (17) illustrates the synthesis of the diphenyl ester (118) of (l-amino-2-propenyl)phosphonic acid (119), an... 

DIETHYL (R)-(-)-(1-AMINO-3-METHYLBUTYL)PHOSPHONATE PHOSPHONIC ACID, (1-AMINO-3-METHYLBUTYL)-, DIETHYL ESTER, (R)- ... 

Diethyl (R)-(-)-[1 -((N-(R)-(1 -phenyl-2-methoxyethyl)amino)-3-methylbutyl)]-phosphonate Phosphonic acid, [1-(2-methoxy-1-phenylethyl)amino]-3-methylbutyl]-, diethyl ester, [R-(R, R )]- (159117-09-6), 75, 20... 

Fields EK (1952) The synthesis of esters of substituted amino phosphonic acids. J Am Chem Soc 74(6) 1528-1531... 

Pudovik AN (1952) Addition of dialkyl phosphites to imines. New method of synthesis of esters of amino phosphonic acids. Dokl Akad Nauk SSSR 83 865-868... 

The title phosphonate and related substances undergo thermal decomposition to B-acyl ketenes at temperatures in excess of 50°C. Thus thermolysis in the presence of alcohols, amines, a-hydroxy esters, and a-amino esters affords the corresponding g-keto esters and amides the latter two classes can be cyclized upon subsequent base treatment to unsaturated tetronic and tetramic acids and the related phosphonate reagents. ... 

Peptides with C-terminal phosphonates, initially reported to have antibacterial properties, have also been found to possess inhibitory properties toward serine proteases)28 The synthesis of peptide phosphonates (Section 15.1.8) usually requires protection of the phos-phonic moiety as a diester, followed by selective deprotection in the final stage. The importance of peptide thiols (Section 15.1.9) is exemplified by captopril, an orally active angiotensin converting enzyme inhibitor used as a treatment for hypertension)29 These peptide thiols are prepared by the reaction of sulfanylalkanoyl amino acids with a-amino esters followed by deprotection of carboxy and sulfanyl groups. Other peptide thiols have been reported to be inhibitors of zinc metalloproteases, collagenases, and aminopeptidases. 

The methodology of the catalytic asymmetric aldol reaction has been further extended to the aldol-type condensation of (isocyanomethyl)phosphonates (12) with aldehydes, providing a useful method for the synthesis of optically active (l-aminoalkyl)phosphonic acids, which are a class of biologically interesting phosphorous analogs of a-amino acids (Scheme 8B1.6) [21,22], Higher enantioselectivity and reactivity are obtained with diphenyl ester 12b than with diethyl ester 12a (Table 8B1.6). 

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