Li–X-type zeolite mediated Michael addition of thiols to cyclic enones and its application in the synthesis of 13-thiaprostaglandins

Shinde, Popat D.; Mahajan, Vishal A.; Borate, Hanumant B.; Tillu, Vasudha H.; Bal, Rajaram; Chandwadkar, A.J.; Wakharkar, Radhika D.

doi:10.1016/j.molcata.2004.02.008

Cited by 19 publications

(7 citation statements)

References 21 publications

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“…The Michael reaction has been recently applied to produce many biologically or pharmacologically active compounds, such as: prostaglandins [64], enzyme inhibitors (3C protease inhibitor [65], cathepsin K cysteine protease inhibitor [66]), potential anti-HIV drugs -(+) Inophyllum B and (+) Calanolide (A) [67], anticancer, antitubercular and antimicrobial agents (cyanopyranes an cyanopyridines [68]), vasopressin receptor V1A and V2 antagonists (spirobenzazepines [69]), peptides [70], antibiotics (semisynthetic macrolides based on Clarithromycin [71]), alkaloids (antimalarial alkaloid (+)-febrifugine [72]), antiepileptic drugs (vigabatrin, GABA aminotransferase inhibitor [73]) and odorants (octahydronaphtalene-based fragrances [74] and trans-magnolione [75]). …”

Section: The Michael Reactionmentioning

confidence: 99%

EMCA and DEEM as Michael Reagents Used in Organic Synthesis

Kaczor¹,

Matosiuk

2005

COC

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Section: The Michael Reactionmentioning

confidence: 99%

EMCA and DEEM as Michael Reagents Used in Organic Synthesis

Kaczor¹,

Matosiuk

2005

COC

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“…Li-exchanged X zeolite has been used as basic catalysts for the preparation of 13-thiaprostaglandins, which are biologically active compounds [244]. These compounds were synthesized through the Michael addition of substituted 3-aryloxy-2- Baba et al [245] prepared basic zeolites consisting of low-valent Yb or Eu species introduced into alkali-ion-exchanged Y zeolites by impregnation with Yb or Eu metal dissolved in liquid ammonia followed by heating under vacuum at about 197 • C. The zeolites thus loaded with Yb or Eu species showed high catalytic activity for the Michael addition between cyclopent-2-enone with dimethyl malonate at 303 K without solvent, yielding after 20 hours the Michael adduct with 81 and 100% selectivity [246,247].…”

Section: Michael Additionmentioning

confidence: 99%

Zeolites as Catalysts for the Synthesis of Fine Chemicals

Climent

Corma

Iborra

2010

Zeolites and Catalysis

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“…However, only limited types of heterogeneous catalysts (including acid and base catalysts) have been applied to this reaction [37][38][39][40][41], partly because this is considered to be more ''energy-demanding'' reaction [42].…”

Section: Introductionmentioning

confidence: 99%

Organic–Inorganic Hybrid Catalysts Based on Ordered Porous Structures for Carbon–Carbon Bond Forming Reactions

2007

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Abstracts Two types of organic-inorganic hybrid base catalysts are prepared. Organic-functionalized molecular sieves (OFMSs); in particular, ''amine-immobilized porous silicates'' are designed based on common idea to immobilize catalytic active sites on silicate surface. Silicateorganic composite materials (SOCMs), such as ''ordered porous silicate-quaternary ammonium composite materials'', are the precursors of ordered porous silicates obtained during the synthesis. Both the OFMS and the SOCM are used as the catalysts for Knoevenagel condensation and Michael addition reactions. Among the OFMSs, there is clear tendency that the use of molecular sieve with larger pore volume and/or surface area gives the product in higher yield. Aminopropylsilyl (AP)-tethered mesoporous silicate such as AP-MCM-41 gives the Knoevenagel condensation product in high yield under mild conditions. No loss of activity is observed after repeated use for three times. The SOCMs are also active for the same reaction. The OFMSs are effective when the supports have large pore volume and/or surface area and the reaction is carried out in polar solvents ethanol and DMF. However, the activity of the OFMSs is considerably low in a non-polar solvent such as benzene. In contrast, the SOCMs are remarkably active in benzene. The organic cation-MCM-41 composite is more active than the composite of an organic cation and a microporous silicate such as zeolite beta and ZSM-12. In the SOCM catalysts, (SiO) 3 SiO -( + NR 4 ) moieties located at the accessible sites are considered to play some important roles. The active species are absent in the liquid phase after the reaction. The recycle of the catalyst was possible without significant loss of activity when the substrates are enough reactive. The mechanism of the reaction over SOCM catalyst is discussed.

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Li–X-type zeolite mediated Michael addition of thiols to cyclic enones and its application in the synthesis of 13-thiaprostaglandins

Cited by 19 publications

References 21 publications

EMCA and DEEM as Michael Reagents Used in Organic Synthesis

EMCA and DEEM as Michael Reagents Used in Organic Synthesis

Zeolites as Catalysts for the Synthesis of Fine Chemicals

Organic–Inorganic Hybrid Catalysts Based on Ordered Porous Structures for Carbon–Carbon Bond Forming Reactions

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