Intramolecular cyclizations of cyclopropenes with indole

Zhu, Peng-Long; Tang, Xiang‐Ying; Shi, Min

doi:10.1039/c6cc02226j

Cited by 18 publications

(4 citation statements)

References 41 publications

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“…Shi et al explored the reactivity of gem -diester substituted cyclopropenes 292 containing a pendant indole core on one of the Csp 2 atoms of the strained carbocycle ( Scheme 37 ) [ 114 ]. They uncovered a Lewis acid-catalyzed cycloisomerization reaction which outcome depended on the substitution of the second Csp 2 of the cyclopropene moiety: when it included a H atom azocino[5,4- b ]indoles 293a were obtained, however when it contained an aryl group tetracyclic (epiminoethano)cyclopenta[ b ]indole derivatives 293b were produced.…”

Section: Synthetic Methodology Involving C–h Functionalization Alomentioning

confidence: 99%

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Azizollahi

Garcı́a-López

2020

Molecules

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The functionalization of C–H bonds has become a major thread of research in organic synthesis that can be assessed from different angles, for instance depending on the type of catalyst employed or the overall transformation that is carried out. This review compiles recent progress in synthetic methodology that merges the functionalization of C–H bonds along with the cleavage of C–C bonds, either in intra- or intermolecular fashion. The manuscript is organized in two main sections according to the type of substrate in which the cleavage of the C–C bond takes place, basically attending to the scission of strained or unstrained C–C bonds. Furthermore, the related research works have been grouped on the basis of the mechanistic aspects of the different transformations that are carried out, i.e.,: (a) classic transition metal catalysis where organometallic intermediates are involved; (b) processes occurring via radical intermediates generated through the use of radical initiators or photochemically; and (c) reactions that are catalyzed or mediated by suitable Lewis or Brønsted acid or bases, where molecular rearrangements take place. Thus, throughout the review a wide range of synthetic approaches show that the combination of C–H and C–C cleavage in single synthetic operations can serve as a platform to achieve complex molecular skeletons in a straightforward manner, among them interesting carbo- and heterocyclic scaffolds.

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Section: Synthetic Methodology Involving C–h Functionalization Alomentioning

confidence: 99%

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Azizollahi

Garcı́a-López

2020

Molecules

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“…For the cyclopropenes 123 bearing an aryl group, a different reaction route was followed, and a kind of tetracyclic product, (epiminoethano)cyclopenta[ b ]indoles 124 were given in high yields (Scheme 21). 34…”

Section: Annulation Reactions Of Commonly Stable Cyclopropenesmentioning

confidence: 99%

Construction of heterocyclic rings from cyclopropenes

Huo

Gong

2022

Org. Biomol. Chem.

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“…158 Subsequently, Shi reported similar reactions using 3,3-diester substituted cyclopropenes 210 prepared from tryptamine derivatives. 159 These compounds in the presence of Brønsted acids evolved through an intramolecular Friedel−Crafts reaction including ring cleavage of three-membered ring to different scaffolds (Scheme 33A). The reaction outcome depended on the substitution at position 2 of the cyclopropene 210.…”

Section: Electrophilic Aromatic Substitution Reactions Using Cyclopro...mentioning

confidence: 99%

“…In 2015, they reported that monoester-substituted cyclopropenes decorated with pedant unprotected indoles could undergo metal-catalyzed cyclizations involving S E Ar reactions without cleaving the cyclopropane backbone . Subsequently, Shi reported similar reactions using 3,3-diester substituted cyclopropenes 210 prepared from tryptamine derivatives . These compounds in the presence of Brønsted acids evolved through an intramolecular Friedel–Crafts reaction including ring cleavage of three-membered ring to different scaffolds (Scheme A).…”

Section: Electrophilic Aromatic Substitution Reactions Using Cyclopro...mentioning

confidence: 99%

C–C Bond Cleavages of Cyclopropenes: Operating for Selective Ring-Opening Reactions

Vicente

2020

Chem. Rev.

139

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This review highlights key reactivities relying on C–C bond cleavages of cyclopropenes. Metal-catalyzed and metal-free transformations are covered in reactions involving direct ring-opening processes or transformations through nonisolable cyclopropane intermediates generated from cyclopropenes. Special emphasis is on the synthetic utility and mechanistic aspects of methodologies discussed along the revision. Different types of reactivities are covered in separate sections including generation of vinyl carbenes and their reactions, metathesis processes, heterocycles syntheses, SEAr reactions, metalation-ring opening sequences, cycloadditions involving ring-cleavages or rearrangements. The focus is on results described from 2007 to the end of 2019, yet relevant pioneering transformations are eventually included.

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Intramolecular cyclizations of cyclopropenes with indole

Cited by 18 publications

References 41 publications

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Construction of heterocyclic rings from cyclopropenes

C–C Bond Cleavages of Cyclopropenes: Operating for Selective Ring-Opening Reactions

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