Highly diastereoselective construction of novel dispiropyrrolo[2,1-a]isoquinoline derivativesviamulticomponent 1,3-dipolar cycloaddition of cyclic diketones-based tetrahydroisoquinoliniumN-ylides

Boudriga, Sarra; Haddad, Saoussen; Askri, Moheddine; Soldera, Armand; Knorr, Michael; Strohmann, Carsten; Golz, Christopher

doi:10.1039/c8ra09884k

Cited by 33 publications

(29 citation statements)

References 72 publications

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“…These 88 structures show many different substitution patterns. The four structures with the most features in common with 1 are probably RAQCIY (Du et al, 2017), IFETAR (Guo et al, 2018), DOHMEV (Boudriga et al, 2019), and KIFRID (Zhang et al, 2018), though none of these are especially similar to 1.…”

Section: Database Surveymentioning

confidence: 99%

Crystal structure of (1′S,2′S,3S)-1′-benzoyl-2′-(4-methoxyphenyl)-1-methyl-2′,5′,6′,10b′-tetrahydro-1′H-spiro[indoline-3,3′-pyrrolo[2,1-a]isoquinolin]-2-one

et al. 2020

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In the title spiro compound, C34H30N2O3, the central pyrrolidine ring is fused with the tetrahydroisoquinoline ring, both having distorted envelope conformations, with the flap atoms being C and N, respectively. The methoxyphenyl group is attached to the pyrrolidine ring, and is disordered over two positions, with refined occupancies of 0.638 (6):0.362 (6) Å. The central pyrrolidine ring is inclined relative to the tetrahydroisoquinoline group, such that the dihedral between the non-flap atoms of each ring system is 11.29 (7)°. The spiro-linkage creates a dihedral angle of 83.26 (5)° between the indolinone ring and the non-flap atoms of the pyrrolidine ring. In the crystal, molecules are linked via C—H...O hydrogen bonds. For the major disorder component, these form C(11) chains that propagate parallel to the a axis.

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Section: Database Surveymentioning

confidence: 99%

Crystal structure of (1′S,2′S,3S)-1′-benzoyl-2′-(4-methoxyphenyl)-1-methyl-2′,5′,6′,10b′-tetrahydro-1′H-spiro[indoline-3,3′-pyrrolo[2,1-a]isoquinolin]-2-one

et al. 2020

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“…After establishing the optimal conditions and screening many substrates, it was found that the regioselectivity (>60 : 40 rr ) was quite poor (Scheme 6). However, the use of halogen substituents, like Cl or Br, in the phenyl ring of isatin were beneficial for increasing regioselectivity (>90 : 10 rr ) in the synthesis of these new dispiropyrrolo[2,1‐ a ]isoquinoline‐fused pyrrolidine‐2,5‐dione derivatives bearing two adjacent spiro‐carbons [22] …”

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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“…Several research groups reported intermolecular (3+2)dipolar cycloadditions of electron-deficient alkenes and azomethine ylides derived from isatins and cyclic amines. [46][47][48][49] In addition to ,-unsaturated alkenes and aldehydes, fullerenes [50][51][52] and ,-unsaturated alkynes 53 are also viable dipolarophiles in (3+2) cycloadditions with azomethine ylides derived from the condensation of cyclic amines and aldehydes.…”

Section: Review Synthesismentioning

confidence: 99%

Condensation-Based Methods for the C–H Bond Functionalization of Amines

Chen

Seidel

2021

Synthesis

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This review aims to provide a comprehensive overview of condensation-based methods for the C–H bond functionalization of amines that feature azomethine ylides as key intermediates. These transformations are typically redox-neutral and share common attributes with classic name reactions such as the Strecker, Mannich, Friedel−Crafts, Pictet−Spengler, and Kabachnik−Fields reaction, while incorporating a redox-isomerization step. This approach provides an ideal platform to rapidly transform simple starting materials into complex amines.

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Highly diastereoselective construction of novel dispiropyrrolo[2,1-a]isoquinoline derivativesviamulticomponent 1,3-dipolar cycloaddition of cyclic diketones-based tetrahydroisoquinoliniumN-ylides

Abstract: A new series of dispiropyrrolo[2,1-a]isoquinoline derivatives was synthesized by multicomponent 1,3-dipolar cycloaddition reaction of tetrahydroisoquinolinium N-ylides and (E)-3-arylidene-1-phenyl-pyrrolidine-2,5-diones.

Cited by 33 publications

References 72 publications

Crystal structure of (1′S,2′S,3S)-1′-benzoyl-2′-(4-methoxyphenyl)-1-methyl-2′,5′,6′,10b′-tetrahydro-1′H-spiro[indoline-3,3′-pyrrolo[2,1-a]isoquinolin]-2-one

Crystal structure of (1′S,2′S,3S)-1′-benzoyl-2′-(4-methoxyphenyl)-1-methyl-2′,5′,6′,10b′-tetrahydro-1′H-spiro[indoline-3,3′-pyrrolo[2,1-a]isoquinolin]-2-one

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

Condensation-Based Methods for the C–H Bond Functionalization of Amines

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