Solvent-free protocol for amide bond formation via trapping of nascent phosphazenes with carboxylic acids

Tetrahedron Letters

Volumn 52, Issue 22, 2011, Pages 2830-2833

  Sathishkumar, Murugan ^a   Shanmugavelan, Poovan ^a   Nagarajan, Sangaraiah ^a   Maheswari, Murugesan ^a   Dinesh, Murugan ^a   Ponnuswamy, Alagusundaram ^a  

^a MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

Amide; MW irradiation Glycerol bath; Solvent free

Indexed keywords

AMIDE; ANTINEOPLASTIC AGENT; CARBOXYLIC ACID; SOLVENT; TRIMETHOXYCINNAMIC AMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; DRUG SYNTHESIS; HEATING; HUMAN; HUMAN CELL; MICROWAVE IRRADIATION;

EID: 79955559068     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.069     Document Type: Article

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23. 3 (Phosphazenes) at 4.0 ppm and appearance of methine signal of - CHNHCOR (amide) at 4.6 ppm.
24. All carboxylic acids (1a-m) and triphenyl phosphine used are of commercial grade of high purity and preparation of organic azides (2a-d) are presented in Supplementary data.
25. General Procedure: To a well ground intimate mixture of triphenyl phosphine (1.1 mmol) and carboxylic acid, 1 (1.0 mmol) in a microwave vial (10 mL) equipped with a magnetic stirring bar, the organic azide, 2 (1.0 mmol) was added in drops while stirring. Stirring was continued until liberation of nitrogen ceased and the reaction vessel was sealed with a septum. It was then placed into the cavity of a focused monomode microwave reactor (CEM Discover, benchmate) and operated at 180 °C (temperature monitored by a built-in IR sensor), power 80 W for 15 min. The reaction temperature was maintained by modulating the power level of the reactor. Alternatively, the microwave vial with the mixture was conventionally heated around 180 °C by immersing in a preheated glycerol bath for 15 min. The reaction vessel was then cooled to room temperature and the residue subjected to column chromatography on silica (pet ether/ethyl acetate, 87:13). This resulted in the isolation of pure amide, 3 Yield (67-88%).
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