Synthetic Approaches toward the Benzo[a]quinolizidine System. A Review

Pashev, Aleksandar; Burdzhiev, Nikola; Stanoeva, Elena

doi:10.1080/00304948.2016.1234820

Cited by 19 publications

(12 citation statements)

References 110 publications

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“…driven the development of various approaches for its obtaining -based either on isolation from naturally occurring sources or through multistep synthetic routes [6]. The pyrrolo[2,1-a]isoquinoline skeleton is incorporated in a large group of natural compounds such as crispines, trolline, and lamellarins, which are interesting due to their anticancer, antiviral, and antibacterial activities [7,8].…”

Section: Introductionmentioning

confidence: 99%

One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli–Cushman protocol

Pashev

Burdzhiev

Stanoeva

2020

Beilstein J. Org. Chem.

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The Castagnoli–Cushman reaction of 3,4-dihydroisoquinolines with glutaric anhydride, its oxygen and sulfur analogues was investigated as a one-step approach to the benzo[a]quinolizidine system and its heterocyclic analogs. An extension towards the pyrrolo[2,1-a]isoquinoline system was achieved with the use of succinic anhydride. The results are evidence of an unexplored method for the access of the aforementioned tricyclic annelated systems incorporating a bridgehead nitrogen atom. The structures and relative configurations of the new compounds were established by means of 1D and 2D NMR techniques. The reactions between 1-methyldihydroisoquinoline and glutaric, diglycolic and succinic anhydrides yielded unexpected isoquinoline derivatives containing an exocyclic double bond. The compounds prepared bear the potential to become building blocks for future synthetic bioactive molecules.

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Section: Introductionmentioning

confidence: 99%

One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli–Cushman protocol

Pashev

Burdzhiev

Stanoeva

2020

Beilstein J. Org. Chem.

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“…Benzo[a]quinolizidine is a key subunit in numerous natural products and pharmaceuticals, such as Emetine, Tubulosine and Tetrabenazine (Figure 1). [10] Emetine is produced from the ipecac root, and has been used as a drug to induce vomiting and as an anti‐protozoal drug [11] . Tubulosine is also found in the alkaloids of the Ipecac species and has similar biological activity with that of Emetine [12] .…”

Section: Figurementioning

confidence: 99%

“…Tetrabenazine is a drug for the symptomatic treatment of hyperkinetic movement disorders [13] . Since many biologically active molecules contain a benzo[a]quinolizidine unit, the synthesis of benzo[a]quinolizidine derivatives has thus received a great deal of attention [10] . However, a multi‐step procedure is usually required for the formation of the core structures [14]…”

Section: Figurementioning

confidence: 99%

An Efficient Construction of CF₃‐Substituted Spirooxindole‐Fused Benzo[a]quinolizidines by a Three‐Component Cyclization

Chen

et al. 2021

Eur J Org Chem

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Benzo[a]quinolizidine is a key subunit in numerous natural products and pharmaceuticals, and therefore its synthesis has received much attention in resent years. Described herein is a convenient three‐component cyclization for the efficient construction of CF3‐substituted spirooxindole‐fused benzo[a]quinolizidines by using CF3‐propiolate as a building block. This attractive protocol may find great synthetic utility since CF3‐containing complex structures were installed by a one‐step cyclization under mild conditions.

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“…Hartley and co-workers applied a Parham-type cyclization reaction 111,112 during the synthesis of a new cyclic nitrone spin trap bearing a lipophilic cation. The carboxylic acid 307 was first converted into the corresponding acyl azide with DPPA followed by Curtius rearrangement to give isocyanate 308.…”

Section: Parham-type Cyclizationmentioning

confidence: 99%

Acyl Azides: Versatile Compounds in the Synthesis of Various Heterocycles

Balcı

2018

Synthesis

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Carbon–nitrogen bond formation is one of the most important reactions in organic chemistry. Various synthetic strategies for the generation of C–N bonds are described in the literature. For example, primary amines can be easily synthesized by the thermal decomposition of an acyl azide to an isocyanate, i.e. the Curtis rearrangement, followed by hydrolysis; the Curtius rearrangement has been used extensively. Furthermore, the advantage of the Curtius rearrangement is the isolation of acyl azides as well as the corresponding isocyanates. The isocyanates can be converted into various nitrogen-containing compounds upon reaction with various nucleophiles that can be used as important synthons for cyclization, in other words, for the synthesis of heterocycles. Therefore, this review demonstrates the importance of acyl azides not only in the synthesis acyclic systems, but also in the synthesis of various nitrogen-containing heterocycles.1 Introduction2 Synthesis of Acyl Azides2.1 Acyl Azides from Carboxylic Acid Derivatives2.2 Acyl Azides by Direct Transformation of Carboxylic Acids2.3 Acyl Azides from Aldehydes2.4 Carbamoyl Azides from Haloarenes, Sodium Azide, and N-Formylsaccharin3 Mechanism of Formation of Isocyanates4 Synthesis of Diacyl Azides5 Synthetic Applications5.1 Synthesis of Pyrimidinone Derivatives5.2 Dihydropyrimidinone and Isoquinolinone Derivatives5.3 Synthesis of Tetrahydroisoquinoline Skeleton5.4 Synthesis of Five-Membered Heterocycles5.5 Heterocycles Synthesized Starting from Homophthalic acid5.6 Heterocycles Synthesized from 2-(Ethoxycarbonyl)nicotinic Acid5.7 Formation of Aza-spiro Compounds5.8 Parham-Type Cyclization5.9 Diazepinone Derivatives5.10 Synthesis of Pyridine Derivatives5.11 Synthesis of Indole Derivatives6 Miscellaneous7 Conclusion

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Synthetic Approaches toward the Benzo[a]quinolizidine System. A Review

Cited by 19 publications

References 110 publications

One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli–Cushman protocol

One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli–Cushman protocol

An Efficient Construction of CF₃‐Substituted Spirooxindole‐Fused Benzo[a]quinolizidines by a Three‐Component Cyclization

Acyl Azides: Versatile Compounds in the Synthesis of Various Heterocycles

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Synthetic Approaches toward the Benzo[a]quinolizidine System. A Review

Cited by 19 publications

References 110 publications

One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli–Cushman protocol

One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli–Cushman protocol

An Efficient Construction of CF3‐Substituted Spirooxindole‐Fused Benzo[a]quinolizidines by a Three‐Component Cyclization

Acyl Azides: Versatile Compounds in the Synthesis of Various Heterocycles­

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An Efficient Construction of CF₃‐Substituted Spirooxindole‐Fused Benzo[a]quinolizidines by a Three‐Component Cyclization

Acyl Azides: Versatile Compounds in the Synthesis of Various Heterocycles