Potential Hypotensive Compounds: Substituted 3-Aminopropionates and 3-Aminopropionohydroxamic Acids

Biggs, David F.; Coutts, Ronald T.; Selley, Michael L.; Towill, G.A.

doi:10.1002/jps.2600611109

Cited by 7 publications

(2 citation statements)

References 12 publications

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“…Following Micovic's strategy, we started from commercially available potassium monomethyl malonate ( 12 ). The in situ generated mixed anhydride formed with pivaloyl chloride (PivCl) underwent smooth N -acylation of β-amino acid methyl ester 13 , which was prepared beforehand from tert -butyl amine and methyl acrylate by conjugate addition . Amide 14 obtained in 75% yield was treated with sodium hydride in refluxing cyclohexane.…”

Section: Resultsmentioning

confidence: 99%

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Preparation and Intramolecular [2+2]-Photocycloaddition of 1,5-Dihydropyrrol-2-ones and 5,6-Dihydro-1H-pyridin-2-ones with C-, N-, and O-linked Alkenyl Side Chains at the 4-Position

2008

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The 1,5-dihydropyrrol-2-ones 2, 6, 9, and 11 were prepared from methyl tetramates (1a-c), N-Boc-protected tetramic acid (3), or N-Boc-protected tetramic acid bromide (7) in short reaction sequences and in very good overall yields. The homologous 5,6-dihydro-1H-pyridin-2-ones 16, 18, 20, 21, 23, and 27 were prepared along analogous routes starting from piperidin-2,4-dione (19) or from its N-tert-butyl derivative 15. Optimized conditions for the [2+2]-photocycloaddition include the use of dichloromethane as the solvent and an irradiation with a mercury low-pressure lamp (lambda = 254 nm). Upon applying these conditions at ambient temperature, the corresponding intramolecular photocycloaddition products 28-37 were obtained in good yields (52-79%) and with perfect diastereoselectivity. The constitution and configuration of the products was elucidated by NMR-spectroscopy. For the O-tethered substrates 2a and 20, a strong decrease of the photocycloaddition rate with temperature was observed. The effect was less pronounced for N- and C-tethered substrates 6, 9, 23, and 27. The use of a chiral complexing agent to achieve enantioselective reactions appears viable. Complexing agent (-)-38, however, is not suited because of its instability at lambda = 254 nm.

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Section: Resultsmentioning

confidence: 99%

“…Preparation of Starting Materials. 4-Methoxy-pyrrolin-2-one ( 1a ), 1-benzyl-4-hydroxy-1,5-dihydro-pyrrol-2-one ( 1b ), β-amino acid methyl ester 13 , the chiral complexing agent (−)- 38 , and but-3-enyl amine 20 were synthesized according to reported procedures. 5-Bromo-1-pentene and 3-buten-1-ol are commercially available.…”

Section: Methodsmentioning

confidence: 99%

Preparation and Intramolecular [2+2]-Photocycloaddition of 1,5-Dihydropyrrol-2-ones and 5,6-Dihydro-1H-pyridin-2-ones with C-, N-, and O-linked Alkenyl Side Chains at the 4-Position

2008

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Pyridazine Analogues of Biologically Active Compounds, VI^1,2): Pyrido[2,3‐c]pyridazines Structurally Related to Nalidixic Acid

Boamah

Haider

Heinisch

1990

Archiv der Pharmazie

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ChemInform Abstract: POTENTIELL BLUTDRUCKSENKENDE VERBINDUNGEN, SUBSTITUIERTE 3‐AMINOPROPIONSAEUREMETHYLESTER UND 3‐AMINOPROPIONOHYDROXAMSAEUREN

Biggs¹,

Coutts²,

Selley³

et al. 1973

Chemischer Informationsdienst

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Potential Hypotensive Compounds: Substituted 3-Aminopropionates and 3-Aminopropionohydroxamic Acids

Cited by 7 publications

References 12 publications

Preparation and Intramolecular [2+2]-Photocycloaddition of 1,5-Dihydropyrrol-2-ones and 5,6-Dihydro-1H-pyridin-2-ones with C-, N-, and O-linked Alkenyl Side Chains at the 4-Position

Preparation and Intramolecular [2+2]-Photocycloaddition of 1,5-Dihydropyrrol-2-ones and 5,6-Dihydro-1H-pyridin-2-ones with C-, N-, and O-linked Alkenyl Side Chains at the 4-Position

Pyridazine Analogues of Biologically Active Compounds, VI^1,2): Pyrido[2,3‐c]pyridazines Structurally Related to Nalidixic Acid

ChemInform Abstract: POTENTIELL BLUTDRUCKSENKENDE VERBINDUNGEN, SUBSTITUIERTE 3‐AMINOPROPIONSAEUREMETHYLESTER UND 3‐AMINOPROPIONOHYDROXAMSAEUREN

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Potential Hypotensive Compounds: Substituted 3-Aminopropionates and 3-Aminopropionohydroxamic Acids

Cited by 7 publications

References 12 publications

Preparation and Intramolecular [2+2]-Photocycloaddition of 1,5-Dihydropyrrol-2-ones and 5,6-Dihydro-1H-pyridin-2-ones with C-, N-, and O-linked Alkenyl Side Chains at the 4-Position

Preparation and Intramolecular [2+2]-Photocycloaddition of 1,5-Dihydropyrrol-2-ones and 5,6-Dihydro-1H-pyridin-2-ones with C-, N-, and O-linked Alkenyl Side Chains at the 4-Position

Pyridazine Analogues of Biologically Active Compounds, VI1,2): Pyrido[2,3‐c]pyridazines Structurally Related to Nalidixic Acid

ChemInform Abstract: POTENTIELL BLUTDRUCKSENKENDE VERBINDUNGEN, SUBSTITUIERTE 3‐AMINOPROPIONSAEUREMETHYLESTER UND 3‐AMINOPROPIONOHYDROXAMSAEUREN

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Pyridazine Analogues of Biologically Active Compounds, VI^1,2): Pyrido[2,3‐c]pyridazines Structurally Related to Nalidixic Acid