Studies on amino acids and peptides x

Thorsen, M.; Andersen, T. P.; Pedersen, U.; Yde, B.; Lawesson, S.‐O.; Hansen, Holger C.

doi:10.1016/s0040-4020(01)91366-3

Cited by 29 publications

(12 citation statements)

References 8 publications

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“…However, they suffer from the need for a separate activation step and from low atom economy. Alternatively, carboxylic acids can be condensed with amines in the presence of stoichiometric activators such as arylboronic acids, 3 bis[bis(trimethylsilyl)amino]tin(II), 4 titanium tetrachloride, 5 trimethylaluminium, 6 Lawesson's reagent, 7 dimethyl phosphoryl chloride, 8 tetrazoles, 9 benzoxazoles, 10 and oxalates. 11 Unfortunately, each of these reagents has their own disadvantage, being unstable, toxic, expensive or commercially unavailable, and requires the removal of by-products.…”

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confidence: 99%

The Thermal Amidation of Carboxylic Acids Revisited

Gooßen¹,

Ohlmann²,

Lange³

2008

Synthesis

111

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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.

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confidence: 99%

The Thermal Amidation of Carboxylic Acids Revisited

Gooßen¹,

Ohlmann²,

Lange³

2008

Synthesis

111

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“…Synthesis of 5-thioxo-L-proline 48 -≡(CSNH)-Gly-OMe 24 93Boc-Leu-≡(CSNH)-Gly-OMe60 66 Boc-Gly-≡(CSNH)-Val-OMe 49 59 reagent can also be used as a racemizationfree coupling reagent in peptide synthesis [79][80][81]. Scheme 16 shows a selected example of this new coupling reaction.…”

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confidence: 99%

Applications of Lawesson’s Reagent in Organic and Organometallic Syntheses

Jesberger¹,

Davis²,

Barner³

2003

Synthesis

287

158

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This review, including 245 references, describes the application of Lawesson's reagent [2,4-bis(p-methoxyphenyl)-1,3-dithiaphosphetane-2,4-disulfide] LR in organic and organometallic syntheses. Thionations of carbonyl-containing compounds as well as unexpected reactions are shown for different applications (e.g. cyclizations, rerrangements, syntheses of heterocyclic compounds etc.). Syntheses of novel organometallic compounds by LR are also discussed.

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“…13 Amides can be generated from the corresponding carboxylic acids and amines by a variety of methods. The reaction has been carried out by a variety of methods such as anhydride, acid chloride, or via in situ coupling agents such as dicyclohexylcarbodiimide, 14 N,Ncarbonyldiimidazole, 15 benzotriazol-1-yldiethylphosphate(BDP), 16 1,1 -carbonylbis(3-methylimidazo-lium)triflate (CBMIT), 17 Lawesson's reagent, 18 Ti(OBu) 4 , 19 Sn[N(TMS) 2 ] 2 , 20 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ), 21 sulfonylchloride, 22 and N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride. 23 Extending our work on the use of N-halosulfonamides 24 in organic synthesis, we now report a convenient method for the conversion of carboxylic acids into esters and amides using a new, cheap, and easily made reagent, N,N -dibromo-N,N -1,2-ethanediyl bis( p-toluenesulfonamide), or BNBTS ( Figure 1).…”

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confidence: 99%