New strategies for the synthesis of fluorinated vinylogous amidines and β-enamino ketones

被引：53

作者：

Fustero, S ^{[1
]}

de la Torre, MG ^{[1
]}

Pína, B ^{[1
]}

Fuentes, AS ^{[1
]}

机构：

[1] Univ Valencia, Fac Farm, Dept Quim Organ, Valencia 46100, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 15期

关键词：

D O I：

10.1021/jo990392w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of fluorinated imidoyl chlorides 3 with ketimines 1a provides fluorinated 1,3-diimines, which were exclusively isolated as vinylogous amidine tautomers 2 beta, with good yields. Fluorinated beta-enamino ketones 4 are obtained by regioselective hydrolysis of 2. Complementary methods for the synthesis of regioisomeric beta-enamino ketones 4 and 5 are also reported. These methods include the reaction of azaenolates of ketimines with fluorinated esters 6 and reactions of ketone enolates with fluorinated imidoyl chlorides 3. The behavior of these systems in hydrolysis reactions was also tested.

引用

页码：5551 / 5556

页数：6

共 48 条

[11] A VERSATILE ROUTE TO BETA-ENAMINO ESTERS BY ACYLATION OF LITHIUM ENAMINES WITH DIETHYL CARBONATE OR BENZYL CHLOROFORMATE
BARTOLI, G
CIMARELLI, C
DALPOZZO, R
PALMIERI, G
[J]. TETRAHEDRON, 1995, 51 (31) : 8613 - 8622
[12] BEGUE JP, 1996, BIOMEDICAL FRONTIERS, P59
[13] Formation of dihydropyridone- and pyridone-based peptide analogs through aza-annulation of beta-enamino ester and amide substrates with alpha-amido acrylate derivatives
Beholz, LG
Benovsky, P
Ward, DL
Barta, NS
Stille, JR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) : 1033 - 1042
[14] Chiral sulfoxide controlled asymmetric additions to C-N double bond.: An efficient approach to stereochemically defined α-fluoroalkyl amino compounds
Bravo, P
Guidetti, M
Viani, F
Zanda, M
Markovsky, AL
Sorochinsky, AE
Soloshonok, IV
Soloshonok, VA
[J]. TETRAHEDRON, 1998, 54 (42) : 12789 - 12806
[15] Stereoselective additions of alpha-lithiated alkyl-p-tolylsulfoxides to N-PMP(fluoroalkyl)aldimines. An efficient approach to enantiomerically pure fluoro amino compounds
Bravo, P
Farina, A
Kukhar, VP
Markovsky, AL
Meille, SV
Soloshonok, VA
Sorochinsky, AE
Viani, F
Zanda, M
Zappala, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (11) : 3424 - 3425
[16] REACTION OF SOME DIKETONES WITH 5-AMINOLEVULINIC ACID IN ACID-SOLUTION
BUTLER, AR
GEORGE, SD
[J]. TETRAHEDRON, 1993, 49 (32) : 7017 - 7026
[17] A NEW AND EFFICIENT APPROACH TO CYCLIC BETA-ENAMINO ESTERS AND BETA-ENAMINO KETONES BY IODINE-PROMOTED CYCLIZATION
FERRAZ, HMC
DEOLIVEIRA, EO
PAYRETARRUA, ME
BRANDT, CA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) : 7357 - 7359
[18] FILLER R, 1993, BIOMEDICAL ASPECTS F
[19] Interaction of fluoroalkyl-containing beta-diketones with amines
Filyakova, VI
Ratner, VG
Karpenko, NS
Pashkevich, KI
[J]. RUSSIAN CHEMICAL BULLETIN, 1996, 45 (09) : 2163 - 2168
[20] An efficient and simple entry to N-substituted beta-enamino acid derivatives from 2-alkyl-2-oxazolines and 2-alkyl-2-thiazolines
Fustero, S
Navarro, A
Diaz, D
delaTorre, MG
Asensio, A
Sanz, F
Gonzalez, ML
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) : 8849 - 8859

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