Synthesis of novel spiro-condensed 2-amino-4H-pyrans based on 1,2-benzoxathiin-4(3H)-one 2,2-dioxide

Grygoriv, G. V.; Lega, Dmitry A.; Zaprutko, Lucjusz; Gzella, Andrzej; Wieczorek-Dziurla, Ewa; Chernykh, V. P.; Shemchuk, L. A.

doi:10.1007/s10593-019-02450-4

Cited by 8 publications

(5 citation statements)

References 13 publications

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“…42 It commonly leans on forming a tetrasubstituted prespiro-carbon prior to the cyclization step yielding spirocycles, and the strategy can be realized as a cascade process. 55,56 This way may utilize well-established organic reactions and features high flexibility, thus mostly eliminates a drawback of employing peculiar reagents and catalysts. Thereby, we chose step-by-step strategy to bring a practically useful preparation of a series of poorly documented 3-spirocyclic -prolines.…”

Section: Resultsmentioning

confidence: 99%

EFFICIENT MULTIGRAM SYNTHESIS OF 3,3-Spiro-Α-Proline CONTAINING CHIMERAS

Derkach,

Levchenko,

Iermolenko

et al. 2024

Preprint

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A series of novel spirocyclic α-proline building blocks for drug discovery with a spiro conjunction in position 3 of pyrrolidine was prepared by means of two convenient and practical synthetic approaches. Both alternative routes utilize simple and easily available starting materials – cyclic ketones and esters – and comprise 6- and 7-steps, respectively. The methodologies feature several advantages, including exploitation of simple organic chemistry transformations and suitability for preparation of multigram amounts of the target prolines. Approach to other valuable chemicals – spirocyclic pyroglutamic acids – is also discussed.

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Section: Resultsmentioning

confidence: 99%

EFFICIENT MULTIGRAM SYNTHESIS OF 3,3-Spiro-Α-Proline CONTAINING CHIMERAS

Derkach,

Levchenko,

Iermolenko

et al. 2024

Preprint

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“…A series of new spiro-condensed 2-amino-4H-pyrans were synthesized by the three-component interaction of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide (1), malononitrile (111), and cyclic carbonyls 119, 120 in moderate to high yields (Scheme 44) [48]. When ethyl cyanoacetate (114) was used, the target ethyl 2-amino-4H-pyran-3-carboxylate was obtained only for N-ethylisatin.…”

Section: Resultsmentioning

confidence: 99%

1,2-Benzoxathiin-4(3H)-one 2,2-dioxide – an underinvestigated building block with a high synthetic and pharmacological potential: synthesis, chemical properties, biological activity

Hryhoriv

Lega

Shemchuk

2021

J. org. pharm. chem.

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Aim. To analyze the available literature data on the methods of synthesis, chemical transformations and the biological activity of derivatives containing a sultone core – 1,2-benzoxathiin-4(3H)-one 2,2-dioxide – and to show the possibilities of their further use in the construction of new molecular systems with attractive pharmacological properties. Results and discussion. The most widespread method for the synthesis of 1,2-benzoxathiin-4(3H)-one 2,2-dioxides is the cyclization of salicylic acid derivatives. The known chemical transformations of 1,2-benzoxathiin-4(3H)-one 2,2-dioxides deal with all reaction centers of the heterocyclic fragment of the condensed system – C=O and CH2 groups, SO2–O bond, CH2CO fragment as a whole. It should be noted that the oxathiine nucleus is prone to undergo recyclizations. The use of 1,2-benzoxathiin-4(3H)-one 2,2-dioxides in multicomponent transformations still remains hardly explored. The “abnormal” course of some classical transformations involving 1,2-benzoxathiine 2,2-dioxides is also noteworthy. The study of the pharmacological properties of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide derivatives is scarce and mainly based on their structural similarity to the coumarin core, which led to the study of anticoagulant, antimicrobial and antitumor properties for the sultone derivatives. Conclusions. The analysis has shown a limited number of studies in each aspect – approaches to the synthesis of 1,2-benzoxathiin-4(3H)-one 2,2-dioxides, their chemical transformations and the study of their pharmacological activity. In addition to a small number of publications on this heterocyclic system, there have been almost no sultone studies in the last 20 years. Taking this into account 1,2-benzoxathiin-4(3H)-one 2,2-dioxide and its derivatives deserve close attention as objects of research for experimental chemistry and pharmacology.

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“…This was in fact the first application of this reagent in multicomponent reactions. This 3‐MCR of equimolar amounts of the described reagents was carried out in the presence of triethanolamine (TEA) as the catalyst, in refluxing ethanol [111] …”

Section: Spirooxindole Derivativesmentioning

confidence: 99%

“…NEt 3 [56] DBU [58] Na 2 CO 3 [61] DMAP [62] DABCO [81] , [82] , [85] , [157] C 4 (DABCO) 2 .2OH [83] NaOAc [94] , [66] , [110] urea [95] TEA [111] CsF [113] …”

Section: Spirooxindole Derivativesmentioning

confidence: 99%

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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Multicomponent reactions (MCRs) are a valuable tool in diversity‐oriented synthesis. Its application to privileged structures is gaining relevance in the fields of organic and medicinal chemistry. Isatin, due to its unique reactivity, can undergo different MCRs, affording multiple interesting scaffolds, namely oxindole‐derivatives (including spirooxindoles, bis‐oxindoles and 3,3‐disubstituted oxindoles) and even, under certain conditions, ring‐opening reactions occur that leads to other heterocyclic compounds. Over the past few years, new methodologies have been described for the application of this important and easily available starting material in MCRs. In this review, we explore these novelties, displaying them according to the structure of the final products obtained.

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Synthesis of novel spiro-condensed 2-amino-4H-pyrans based on 1,2-benzoxathiin-4(3H)-one 2,2-dioxide

Cited by 8 publications

References 13 publications

EFFICIENT MULTIGRAM SYNTHESIS OF 3,3-Spiro-Α-Proline CONTAINING CHIMERAS

EFFICIENT MULTIGRAM SYNTHESIS OF 3,3-Spiro-Α-Proline CONTAINING CHIMERAS

1,2-Benzoxathiin-4(3H)-one 2,2-dioxide – an underinvestigated building block with a high synthetic and pharmacological potential: synthesis, chemical properties, biological activity

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

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