1,3-Dipolar cycloaddition of imidate ylides on imino-alcohols: Synthesis of new imidazolones using solvent free conditions

Lerestif, Jean Michel; Perrocheau, J.; Tonnard, F.; Bazureau, Jean Pierre; Hamelin, J.

doi:10.1016/0040-4020(95)00321-x

Cited by 51 publications

(30 citation statements)

References 31 publications

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“…of triethylamine were used, the product mixture contained some diaddition material (4). No reaction took place under anhydrous conditions, contrary to a report by Lerestif et al 5 who claimed that anhydrous triethylamine was required. Compound (5b) was also prepared in this manner.…”

Section: Resultscontrasting

confidence: 63%

“…Synthesis of Amino Acid Imidates (5) The use of imidate esters (5) to prepare 4,5-dihydro-1,2,4-triazin-6(1H )-ones has been demonstrated by Kjaer 4 and Camparini et al 2 Imidate derivatives of the type (5) can be prepared from the reaction (Scheme 1) of the corresponding amino acid ester hydrochloride salts (1a,b) with triethylamine and the imidate ester hydrochloride salt (2). 5 A mixture of the amino acid ester hydrochloride salt (1a), methyl benzimidate hydrochloride (2) and 1 equiv.…”

Section: Resultsmentioning

confidence: 98%

“…However, amino acid imidates (5) are usually prepared by the general procedure of Schmidt 6 or by a modification 7 in which an aqueous solution of the amino acid ester hydrochloride (1a-c) is shaken with a diethyl ether solution of the imidate ester (3) (Scheme 1). When ethyl glycinate hydrochloride (1a) was used, the yield of the desired imidate derivative (5a) was relatively low (59%) and it was accompanied by 12% of the hydrolysis product ethyl N -benzoylglycinate (6a) and 29% of unidentified products.…”

Section: Resultsmentioning

confidence: 99%

“…5 A mixture of the amino acid ester hydrochloride salt (1a), methyl benzimidate hydrochloride (2) and 1 equiv. of 'laboratory grade' triethylamine in dichloromethane was stirred at room temperature overnight to give the corresponding amino acid imidate (5a) in 60% yield and 80% purity.…”

Section: Resultsmentioning

confidence: 99%

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Dihydro-1,2,4-triazin-6(1H)-ones. II Synthesis of Several Methylated 3-Phenyl- 4,5-dihydro-1,2,4-triazin-6(1H)-ones

Collins¹,

Hughes²,

Johnson

1999

Aust. J. Chem.

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Novel syntheses of 4,5-dihydro-1,2,4-triazin-6(1H)-ones were developed by use of imidoyl chlorides. The overall yield of 4,5-dihydro-1,2,4-triazin-6(1H)-ones prepared from amino acid imidates and hydrazines was improved by the development of a much more efficient synthesis of the imidates. The new 1,2-, 1,4- and 5,5-dimethyl dihydro-1,2,4-triazin-6(1H)-ones have been synthesized by cyclocondensation/cycloaddition pathways. Base-catalysed methylation of 3-phenyl-4,5-dihydro-1,2,4-triazin-6(1H)-one (15) gave the 1- methylated derivative (8); under similar conditions 2-methyl-3-phenyl-2,5-dihydro-1,2,4-triazin-6(1H)-one (9) afforded the 1,2-dimethyl derivative (7).

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Section: Resultscontrasting

confidence: 63%

Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Dihydro-1,2,4-triazin-6(1H)-ones. II Synthesis of Several Methylated 3-Phenyl- 4,5-dihydro-1,2,4-triazin-6(1H)-ones

Collins¹,

Hughes²,

Johnson

1999

Aust. J. Chem.

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“…Recently, imidate 69 was shown to be in equilibrium by thermal 1,2-prototropy with its corresponding azomethine ylide 71, which can be regarded as a nitrile ylide synthon ( Fig. (15)) [90]. Thus, reactions between 69 and aldehydes, such as 2-furaldehyde, with dry acetic acid as catalyst in the absence of solvent under focused microwave irradiation were investigated [91].…”

Section: Imidazolonesmentioning

confidence: 98%