The Thermal Amidation of Carboxylic Acids Revisited

被引：99

作者：

Goossen, Lukas J. ^{[1
]}

Ohlmann, Dominik M. ^{[1
]}

Lange, Paul P. ^{[1
]}

机构：

[1] Tech Univ Kaiserslautern, Fachbereich Chem, D-67663 Kaiserslautern, Germany

来源：

SYNTHESIS-STUTTGART | 2009年 / 01期

关键词：

amides; amines; condensation; molecular sieves; CONVENIENT SYNTHESIS; PEPTIDE-SYNTHESIS; AMIDES; DERIVATIVES; CONVERSION; CARBOXAMIDES; AMINES; ACTIVATION; REAGENTS; CATALYST;

D O I：

10.1055/s-0028-1083277

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Factors affecting the thermal condensation of carboxylic acids with amines have been investigated, and an effective protocol for this waste-minimized, environmentally benign transformation has been identified. Fourteen examples demonstrate the applicability of this procedure to aliphatic, aromatic and heteroaromatic carboxylic acids and primary and secondary aliphatic as well as aromatic amines. The approach leads to the corresponding amides in good yields.

引用

页码：160 / 164

页数：5

共 34 条

[1] CYCLIZATION OF 9-SUBSTITUTED DECANOIC ACID-DERIVATIVES TO 9-DECANOLIDE AND 9-DECANELACTAM
BARTRA, M
VILARRASA, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17) : 5132 - 5138
[2] Beckwith A.L. J., 1970, Synthesis of amides, P105
[3] THE CONVERSION OF CARBOXYLIC-ACIDS TO AMIDES VIA TIN(II) REAGENTS
BURNELLCURTY, C
ROSKAMP, EJ
[J]. TETRAHEDRON LETTERS, 1993, 34 (33) : 5193 - 5196
[4] Copper-catalyzed N-arylation of amines/amides in poly(ethylene glycol) as recyclable solvent medium
Chandrasekhar, S
Sultana, SS
Yaragorla, SR
Reddy, NR
[J]. SYNTHESIS-STUTTGART, 2006, (05): : 839 - 842
[5] A CONVENIENT SYNTHESIS OF AMIDES FROM CARBOXYLIC-ACIDS AND PRIMARY AMINES
COSSY, J
PALEGROSDEMANGE, C
[J]. TETRAHEDRON LETTERS, 1989, 30 (21) : 2771 - 2774
[6] DI-TERT-BUTYL N-ACYLIMIDODICARBONATES AS ISOLABLE ACYLATING AGENTS - MILD CONVERSION OF PRIMARY CARBOXAMIDES TO SUBSTITUTED AMIDES
DAVIDSEN, SK
MAY, PD
SUMMERS, JB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) : 5482 - 5485
[7] FLERZDAVID HE, 1939, HELV CHIM ACTA, V22, P579
[8] New role for urea as a surfactant headgroup promoting self-assembly in water
Fong, C
Wells, D
Krodkiewska, I
Hartley, PG
Drummond, CJ
[J]. CHEMISTRY OF MATERIALS, 2006, 18 (03) : 594 - 597
[9] Dual Si-H effects in platinum-catalyzed silane reduction of carboxamides leading to a practical synthetic process of tertiary-amines involving self-encapsulation of the catalyst species into the insoluble silicone resin formed
Hanada, Shiori
Motoyama, Yukihiro
Nagashima, Hideo
[J]. TETRAHEDRON LETTERS, 2006, 47 (35) : 6173 - 6177
[10] Heyde C, 2000, EUR J ORG CHEM, V2000, P3273

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