Synthesis of spiropyrrolidines: 1,3-dipolar cycloaddition reactions of an azomethine ylide to unusual dipolarophiles; a molecular orbital study of the cycloaddition reaction

Raj, A. Amal; Raghunathan, R.; Malar, E. J. Padma

doi:10.1002/(sici)1098-1071(1999)10:6<500::aid-hc11>3.0.co;2-m

Cited by 11 publications

(1 citation statement)

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“…[85] Raj et al (1999) reported the synthesis of a series of spiro[chromane-3,3'-pyrrolidin]-4-one via regioselective 1,3-dipolar cycloaddition reactions of in-situ generated azomethine ylides (obtained by thermolysis of 3-aroyl aziridines) and dipolarophile (E)-3-arylidene 4-chromanones. [86] A solution of cis-1-cyclohexyl-2-phenyl-3-benzoylaziridine 76 and substituted (E)-3-arylidene-4-chromanones 1 in dry toluene furnished the single cycloadduct 1-cyclohexyl-2-phenyl À 3-aryl-5-benzoylpyrrolidine-spiro[4.3']-4-chromanones 77 (Scheme 28), containing four contiguous chiral centres in moderate to excellent yields.…”

Section: Spiro[chromane-33'-pyrrolidin]-4-onesmentioning

confidence: 99%

3‐Arylidene‐4‐Chromanones and 3‐Arylidene‐4‐Thiochromanones: Versatile Synthons towards the Synthesis of Complex Heterocycles

2022

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Heterocyclic compounds are well-known for their use in the synthesis of drugs and drug intermediates. This review provides a systematic survey on the chemical synthesis of complex heterocyclic compounds containing multistereocentres using 3-arylidene-4-chromanones in the last two decades. Regioselective and stereoselective synthesis of complex heterocycles involving 3-arylidene-chromanones and 3-arylidene-thiochormanones are dealt under various reaction headings such as epoxidation, Michael addition, 1,3dipolar cycloaddition, [3 + 2] and [4 + 2] cycloaddition, Diels-Alder reaction, sulfa-Michael/aldol cascade reactions, asym-metric synthesis employing bifunctional catalysts, chiral phase-transfer catalysts, chiral squaramide catalysts, etc. These synthetic highlights demonstrate the utility of 3arylidene-4-chromanones and 3-arylidene-thiochormanones as versatile synthons for rapid assemblage of complex condensed heterocyles and spiro-fused heterocycles towards the development of pharmaceutically active compounds. A brief highlight on the synthetic methods of 3-arylidene-4chromanone derivatives is also dealt. This review creates a platform for further improvement on the skeletal design of potential drug candidates.

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Section: Spiro[chromane-33'-pyrrolidin]-4-onesmentioning

confidence: 99%