Design and synthesis of<i>C</i><sub>3</sub>-symmetric molecules bearing propellane moieties via cyclotrimerization and a ring-closing metathesis sequence

Kotha, Sambasivarao; Todeti, Saidulu; Aswar, Vikas R.

doi:10.3762/bjoc.14.230

Cited by 7 publications

(8 citation statements)

References 46 publications

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“…step protocol starting with 2,3-dihydro-1H-inden-1-one (60), which was treated with allyl bromide (14) in the presence of NaH to obtain the diallyl indanones 61 (Scheme 13). The RCM sequence of diallyl indanones 61 with the aid of G-I catalyst gave the corresponding spiro-indanones 62a-d in good yields.…”

Section: Account Synlettmentioning

confidence: 99%

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Modular Approaches to Cyclopentanoids and their Heteroanalogs

Kotha

Tangella²

2020

Synlett

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Cyclopentanoids and their derivatives are interesting targets in synthetic organic chemistry due to their extensive applications in various branches of chemical sciences like pharmaceuticals, natural and non-natural products. In view of these applications, several synthetic strategies have been developed in the past three to four decades. In this article, we describe our work towards the synthesis of cyclopentanoids and their heteroanalogs involving diverse synthetic strategies during the past two decades. Among these, photo-thermal olefin metathesis, ring-closing metathesis, ring-rearrangement metathesis, cyclopentane annulation, [2+2+2] cycloaddition, and Diels-Alder reactions have been used to assemble cyclopentane rings of diverse architecture.

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Section: Account Synlettmentioning

confidence: 99%

“…Further, a sequence of allylation followed by RCM with G-II catalyst provided the N-containing C 3 -symmetric molecule 167 bearing a propellane moiety in 87% yield (Scheme 34). 60 Very recently, Kotha…”

Section: Account Synlettmentioning

confidence: 99%

Modular Approaches to Cyclopentanoids and their Heteroanalogs

Kotha

Tangella²

2020

Synlett

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“…cis-(2-Benzyloctahydrocyclopenta [c]pyrrole-3a,6a-diyl)dimethanol (32). Compound 26 (244 g, 1.03 mol) was added to a solution of alkene 30 (141 g, 1.02 mol) in CH 2 Cl 2 (700 mL).…”

Section: ■ Experimental Partmentioning

confidence: 99%

Far Away from Flatland. Synthesis and Molecular Structure of Dihetera[3.3.n]propellanes and Trihetera[3.3.n]propellanes: Advanced Analogues of Morpholine/Piperazine

et al. 2019

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An approach to di- and trihetera[3.3.n]propellanes (n = 2–4 ), advanced morpholine and piperazine analogues, is developed. The key step of the reaction sequence included a [3 + 2] cycloaddition reaction of unsaturated vicinal dicarboxylic acid derivatives and in situ generated azomethine ylide resulting in the formation of the pyrrolidine ring. One more heteroaliphatic ring (i.e., pyrrolidine or tetrahydrofuran) was annelated by nucleophilic cyclization of the appropriate 1,4-dielectrophilic intermediates. There were 11 examples of the title products obtained in 3–5 steps on a multigram scale with 10–72% overall yields. Additionally, molecular structures of homologous dihetera[3.3.n]propellanes, analogues of morpholine, were obtained from X-ray diffraction studies and analyzed using exit vector plots (EVPs). It was shown that the scaffolds obtained are somewhat larger as compared to the parent morpholine and bicyclic 3-oxa-7-azabicyclo[3.3.0]octane. Moreover, despite very similar chemical structures, they provide a very distinct spatial position of heteroatoms, which is clearly seen from the conformation adopted by a formal eight-membered ring including both N and O atoms (i.e., crown, boat–chair, twist chair–chair, and boat–boat for the oxaza[3.3.2]-, -[3.3.3]-, -[4.3.3]propellanes, and 3-oxa-7-azabicyclo[3.3.0]octane, respectively).

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“…Kotha and co‐workers developed a simple route to advanced star‐shaped molecules that contained three propellane moieties at their peripheries . Star‐shaped molecule 186 was synthesized in a three‐step sequence (Scheme ).…”

Section: Carbon−carbon Bond Formationmentioning

confidence: 99%

“…Kotha and co-workers developed as imple route to advanceds tar-shaped molecules that containedt hree propellane moieties at their peripheries. [42] Star-shaped molecule 186 was synthesized in at hree-step sequence (Scheme 56). First, the Diels-Alder reaction between cyclopentadiene (182)a nd maleic anhydride (183)g ave the well-known endo adduct 184 (98 %y ield), whichw as transformed into the desired acetyl derivative( 185)b yc ondensation with 4-acetylaniline (173).…”

Section: Metathesis Reactionsmentioning

confidence: 99%

Synthetic Approaches to Star‐Shaped Molecules with 1,3,5‐Trisubstituted Aromatic Cores

Kotha

Meshram

Panguluri

et al. 2019

Chemistry An Asian Journal

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Herein, we summarize the synthetic approaches that have been developed for the synthesis of star‐shaped molecules. Typically, to design such highly functionalized molecules, simple building blocks are first assembled through trimerization reactions, starting from commercially available starting materials. Then, these building blocks are synthetically manipulated to generate extended star‐shaped molecules. We also discuss the syntheses of star‐shaped molecules that contain 2,4,6‐trisubstituted 1,3,5‐triazine or 1,3,5‐trisubstituted benzene rings as a central core and diverse substituted styrene, phenyl, and fluorene derivatives at their periphery, which endows these molecules with extended conjugation. A variety of metal‐catalyzed reactions, such as Suzuki, Buchwald–Hartwig, Sonogashira, Heck, and Negishi cross‐coupling reactions, as well as metathesis, have been employed to functionalize a range of star‐shaped molecules. The methods described herein will be helpful for designing a wide range of intricate compounds that are highly valuable in the fields of supramolecular chemistry and materials science. Owing to space limitations, we will not cover all of the publications on this topic. Instead, we will focus on examples that were reported by our research group and other relevant recent literature. Apart from the trimerization sequence, this Minireview has been structured based on the key reactions that were used to prepare the star‐shaped molecules and other higher analogues. Finally, some examples that do not fit into this classification are discussed.

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Design and synthesis ofC₃-symmetric molecules bearing propellane moieties via cyclotrimerization and a ring-closing metathesis sequence

Cited by 7 publications

References 46 publications

Modular Approaches to Cyclopentanoids and their Heteroanalogs

Modular Approaches to Cyclopentanoids and their Heteroanalogs

Far Away from Flatland. Synthesis and Molecular Structure of Dihetera[3.3.n]propellanes and Trihetera[3.3.n]propellanes: Advanced Analogues of Morpholine/Piperazine

Synthetic Approaches to Star‐Shaped Molecules with 1,3,5‐Trisubstituted Aromatic Cores

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Design and synthesis ofC3-symmetric molecules bearing propellane moieties via cyclotrimerization and a ring-closing metathesis sequence

Cited by 7 publications

References 46 publications

Modular Approaches to Cyclopentanoids and their Heteroanalogs

Modular Approaches to Cyclopentanoids and their Heteroanalogs

Far Away from Flatland. Synthesis and Molecular Structure of Dihetera[3.3.n]propellanes and Trihetera[3.3.n]propellanes: Advanced Analogues of Morpholine/Piperazine

Synthetic Approaches to Star‐Shaped Molecules with 1,3,5‐Trisubstituted Aromatic Cores

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Design and synthesis ofC₃-symmetric molecules bearing propellane moieties via cyclotrimerization and a ring-closing metathesis sequence