Synthesis of Phenanthridine Derivatives Functionalized in the C‐Ring by Means of IMDAF Reactions under Microwave or Conventional Heating Conditions

Gulbrandsen, Håkon Sætren; Hennum, Martin; Osheka, Maksim; Read, Matthew Lovell; Gundersen, Lise‐Lotte

doi:10.1002/ejoc.201403111

Eur J Org Chem

2014

DOI: 10.1002/ejoc.201403111

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Synthesis of Phenanthridine Derivatives Functionalized in the C‐Ring by Means of IMDAF Reactions under Microwave or Conventional Heating Conditions

Håkon Sætren Gulbrandsen

Martin Hennum

Maksim Osheka

et al.

Abstract: Phenanthridines functionalized in the C-ring have been synthesized by IMDAF (intramolecular Diels-Alder reaction on furans) cyclization of ortho-furyl(alkenylamino)arenes under both microwave and conventional heating conditions. The outcomes of the reactions are highly dependent on the substitution patterns both on the dienophile and on the arene components. 5,6-Dihydrophenanthridines, which can easily be oxidized to fully aromatic phenanthridines, are formed

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Cited by 9 publications

References 30 publications

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A One‐Pot Approach to Phenanthridine Derivatives through Two‐Step Rhodium(I) and Gold(I) Catalysis

Zhu

Chen

et al. 2015

Adv Synth Catal

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An effectiveo ne-pot procedure for the synthesis of phenanthridine derivatives containing N-or O-heterocycles has been developed through at wo-stepr hodium-catalyzed[ 2 + +2+ +2] cycloaddition and gold-catalyzedh eterocyclization under mild conditions.T he substrate scope has been investigated and ap lausible reactionm echanism has been proposed on the basis of control experiments and previousl iterature reports.Keywords: [2+ +2+ +2] cycloaddition;g old catalysis; heterocyclization;o ne-pot procedure;r hodium catalysis Polycyclicc ompounds containingN -a nd O-heterocycles are the core structures in av ariety of pharmacologicala gents and natural alkaloids.[1] Thus far, the development of new synthetic methodso rs trategies for heterocyclic compounds hasbeenavery important area in organic synthesis.[2] Recently,t he synthesiso f substituted or functionalized phenanthridines hasa ttracted much attention sincet hey are the core structural motifsi nm anyb iologically active molecules as shown in Figure 1, andn ew synthetic protocols for these compounds are stillh ighly desirable. [3] Over the past decades,s ynthesis of polycyclic compounds has made significant progress and al arge number of useful andpractical methodshavebeen explored, in which transition metal catalysish as been playing av ery important role.W ith the aid of transition metal catalysis, one can rapidly generate complex molecular structures from easily accessible starting materials under mild reaction conditions.F or example,t he transitionm etal-catalyzed [2+ +2+ +2] cycloaddition reactions of unsaturated compounds are very useful and straightforward methods for constructing polycyclic compounds.[4] Various highly regioselective [2+ +2+ +2] cycloadditions of diynes under Co,N i, Ir, Ru, Au or Rh catalysis have been reported by several groups.[5-10] Furthermore,heterocyclizations of alkynes under transitionm etal catalysis are also practical and straightforward methodst oc onstruct heterocyclic compounds. [11][12][13][14][15][16][17][18] Nowadays,o ne-pot synthesis is becoming an importants trategys incei tc an improve the efficiency of ac hemical reaction. Theo ne-pot reactions combiningt ransitionm etal catalysis ando rganocatalysis leadt om anye legant and effective synthetic protocols. [19,20] On the basis of this strategy,m ultistep chemical transformationsc an be performed sequentially to givec omplexm olecules in as ingle reaction vessel,s ubsequently reducing work-up and purification steps.Recently,t he reactions catalyzed by gold complexes have been exploreds ignificantly.M oreover, some examples about gold-catalyzed cascade reactions and dual-metal catalysisw ith gold ands econd metals have

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A One‐Pot Approach to Phenanthridine Derivatives through Two‐Step Rhodium(I) and Gold(I) Catalysis

Zhu

Chen

et al. 2015

Adv Synth Catal

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Hantzsch Ester‐Mediated Synthesis of Phenanthridines under Visible‐Light Irradiation

Nagode

Kant

Rastogi

2020

Chemistry An Asian Journal

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An efficient photocatalytic synthesis of phenanthridines mediated by an organo-photoredox initiator Hantzsch ester has been developed via denitrogenative intramolecular annulation of benzotriazolyl chalcones. The highly reducing photoactivated Hantzsch ester facilitates the transformation of benzotriazolyl chalcones into phenanthridinyl chalcones through photoinduced electron transfer (PET) and hydrogen atom transfer (HAT) processes. The mild reaction conditions utilizing inexpensive Hantzsch ester as photosensitizer, wide reaction scope and excellent functional group tolerance are notable attributes of the methodology.

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ChemInform Abstract: Synthesis of Phenanthridine Derivatives Functionalized in the C‐Ring by Means of IMDAF Reactions under Microwave or Conventional Heating Conditions.

et al. 2015

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The results of the intramolecular reactions of substrates (I) and (VII) are highly dependent on the substituents and on the reaction conditions. Initially formed Diels-Alder adducts such as (III) and (VIII) are transformed into alcohols, ketones, or oxidized to fully aromatic phenanthridine (VI). -(GULBRANDSEN, H. S.; HENNUM, M.; OSHEKA, M.; READ, M. L.; GUNDERSEN*, L.-L.; Eur. J. Org. Chem. 2014, 36, 8182-8190, http://dx.

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Synthesis of Phenanthridine Derivatives Functionalized in the C‐Ring by Means of IMDAF Reactions under Microwave or Conventional Heating Conditions

Cited by 9 publications

References 30 publications

A One‐Pot Approach to Phenanthridine Derivatives through Two‐Step Rhodium(I) and Gold(I) Catalysis

A One‐Pot Approach to Phenanthridine Derivatives through Two‐Step Rhodium(I) and Gold(I) Catalysis

Hantzsch Ester‐Mediated Synthesis of Phenanthridines under Visible‐Light Irradiation

ChemInform Abstract: Synthesis of Phenanthridine Derivatives Functionalized in the C‐Ring by Means of IMDAF Reactions under Microwave or Conventional Heating Conditions.

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