Microwave-Assisted Solid-Phase Synthesis of Phthalimides

Martin, Bénédicte; Sekljic, Harald; Chassaing, Christophe

doi:10.1021/ol0343818

Cited by 39 publications

(20 citation statements)

References 13 publications

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“…A number of related microwaveassisted cyclative-release protocols have been reported. [223,224] Apart from traditional cross-linked polystyrene resins a number of different supports and formats have been used in microwave-assisted SPOS. These include tentagel resins, [117,213,214,225] cellulose membranes (SPOT synthesis), [226,227] cellulose beads, [228] and glass surfaces.…”

Section: Methodsmentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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Although fire is now rarely used in synthetic chemistry, it was not until Robert Bunsen invented the burner in 1855 that the energy from this heat source could be applied to a reaction vessel in a focused manner. The Bunsen burner was later superseded by the isomantle, oil bath, or hot plate as a source for applying heat to a chemical reaction. In the past few years, heating and driving chemical reactions by microwave energy has been an increasingly popular theme in the scientific community. This nonclassical heating technique is slowly moving from a laboratory curiosity to an established technique that is heavily used in both academia and industry. The efficiency of “microwave flash heating” in dramatically reducing reaction times (from days and hours to minutes and seconds) is just one of the many advantages. This Review highlights recent applications of controlled microwave heating in modern organic synthesis, and discusses some of the underlying phenomena and issues involved.

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Section: Methodsmentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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“…Chassaing et al have developed a traceless solid-phase synthesis of N-substituted phthalimide libraries. 132 The synthetic route involves the use of the Wang resin loaded with phthalic acid employing the Mitsunobu protocol. Subsequent reaction with alkyl or aralkyl amines under standard amide coupling conditions led to the generation of resin-bound N-alkyl or benzylphthalamic acids.…”

Section: Scheme 28mentioning

confidence: 99%

Microwave-promoted synthesis of cyclic imides

Perillo¹,

Shmidt²,

Prieto³

et al. 2018

Arkivoc

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Cyclic imides have been extensively investigated because of the wide range of biological activities they exert, as well as due to their importance as synthetic intermediates. Nowadays, focus has been placed on this important class of compounds for their potential new applications, especially in the area of pharmaceutical chemistry. Consequently, the strategies applied for the synthesis of these compounds have attracted considerable attention. Several innovative methodologies have been developed to obtain and functionalize this class of compounds. The use of microwave heating, which is an environmentally harmless strategy, has been making successful inroads in many chemistry areas, such as organic synthesis. Herein we present an update of the microwave-promoted methods for the synthesis of cyclic imides.

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“…Kappe and Stadler have shown that PS resins tolerate microwave heating up to temperatures of 200 • C [38]. A wide variety of successful microwave-assisted transformations on PS support has been reported [37,38,[49][50][51][52][53][54][55][56][57][58][59][60][61][62][63][64][65][66][67][68].…”

Section: Insoluble Polymer Supportsmentioning

confidence: 99%

“…A related microwave-assisted cyclative cleavage strategy was proposed for the synthesis of substituted phthalimide libraries by Chassaing et al [60]. It should be noted that protocols using conventional heating [167,168] were found to be unfeasible for large library production, as they required reaction times of several hours.…”

Section: Phthalimide Library Synthesis On Wang Resinmentioning

confidence: 99%