A Convenient Approach to the Synthesis of Furo- and Thieno-[3,2-c]pyridine Derivatives

Maruoka, Hiroshi; Okabe, Fumi; Yamasaki, Keishi; Masumoto, Eiichi; Fujioka, Toshihiro; Yamagata, Kenji

doi:10.3987/com-10-s(e)47

Cited by 6 publications

(1 citation statement)

References 31 publications

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“…Furo[3,2- c ]pyridines play an important role in organic chemistry for their presence in numerous natural products and synthetic organic compounds along with diverse bio-, physio-, and pharmacological activities. , In addition, furo[3,2- c ]pyridines are common organic ligands in transition metal complexes . Extensive work has generated many synthetic approaches to furo[3,2- c ]pyridine derivatives, starting either from preformed furans or pyridines. , However, most of the existing methods require multistep procedures to generate the pyridine and furan rings individually, and suffer from limited substrate scope and harsh reaction conditions. So far, there are only very few methods reported on the synthesis of furo[3,2- c ]pyridines by construction of the furan and pyridine nuclei in a single step .…”

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[5C + 1N] Annulations: Two Novel Routes to Substituted Dihydrofuro[3,2-c]pyridines

et al. 2012

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Two novel routes based on [5C + 1N] annulations for the synthesis of 2,3-dihydrofuro[3,2-c]pyridines are described. Ammonium acetate (NH(4)OAc) is used as an ammonia source in both routes. The first route utilizes 1-acyl-1-[(dimethylamino)alkenoyl]cyclopropanes as a five-carbon 1,5-bielectrophilic species and combines the [5C + 1N] annulation and regioselective ring-enlargement of cyclopropyl ketone into one pot, whereas the second route utilizes 3-acyl-2-[(dimethylamino)alkenyl]-4,5-dihydrofurans as the five-carbon synthons, which involves a sequential intermolecular aza-addition, intramolecular aza-nucleophilic addition/elimination, and dehydration reaction.

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[5C + 1N] Annulations: Two Novel Routes to Substituted Dihydrofuro[3,2-c]pyridines

et al. 2012

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Brønsted Acid‐Promoted Cascade Alkylation/Cyclization of Pyrroles with N,N‐Dimethylaminomethyleneglutaconic Acid Dinitrile: A Concise Route to Cyclopenta[b]pyrroles

Chen

et al. 2015

Adv Synth Catal

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AB r ønsted acid (p-TsOH·H 2 O) promoted alkylation/cyclization cascade reactiono fp yrroles with N,N-dimethylaminomethyleneglutaconic acid dinitrile was efficiently realized to afford functionalized cyclopenta [b]pyrroles with excellent diastereoselectivity.D eamination of the corresponding ammonium saltso ft he cyclopenta [b]pyrroles with methyl iodide led to dihydrocyclopenta[c]pyrroles. Thec ascade reactionp athway was confirmed by isolation and transformation of the reactioni ntermediate,i .e., the 2-alkylated pyrrole.Keywords: Brønsted acid;c yclization; cyclopenta [b]pyrroles; N,N-dimethylaminomethyleneglutaconic acid dinitrile;pyrroles Fused heterocyclic compoundsc ontainingacyclopenta [b]pyrrole motif are present in many biologically active natural products andm edicinallyi mportant compounds, [1] such as,k rill fluorescent substance F [2] which is ac omponent of the phorbine chromophore presenti na ll types of chlorophylls,r oseophilin, [1c,3] and an inhibitor of d-amino oxidase [4] (Figure 1). Consequently,m uch effort has recentlyb een devoted to the synthesis of cyclopenta [b]pyrrole derivatives.T he acid-mediated Nazarov cyclization is au seful method for the constructiono ff ive-membered carbocycles, [5] which has usuallyb een employed as as traightforward route to access cyclopentenone-fused pyrroles.[6] Tr ansition metal-catalyzed cyclization/ring expansion of functionalized alkynes, [7] hydroformylation of 1,4-dienes followed by condensation with primary amines, [8] and other reactions [9] have also been applied for the synthesis of cyclopenta[b]pyrrole derivatives.Brønsted or Lewis acid-promoted Friedel-Crafts cyclization has been considereda sapowerful method to prepare heterocyclic compounds.[10] Ap yrrole ring can thusb eu sed as the "template"-like structure to establish another ring onto it for the construction of polycyclic compounds, [11] in which annulation of prefunctionalized alkynes or olefins to ap yrrole core is usuallyi nvolved. After screening of the relevant known synthetic methods, we reasonedt hat ad iene might be utilized to replace the pre-functionalized alkyneso ro lefins for the same purpose.T he polarized diene, N,N-dimethylaminomethyleneglutaconic acid dinitrile, [12] which is structurally endowedw ith an electron-donating NMe 2 moiety andt wo electronwithdrawing cyano groups attacheda ti ts two C=C bonds,h as been useda saC 3 building block to synthesize carbocyclic compounds.[13] Recently,w ef ound that Brønsted acids could promote Friedel-Crafts alkylationo fi ndoles with N,N-dimethylaminomethy-

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ChemInform Abstract: A Convenient Approach to the Synthesis of Furo‐ and Thieno‐[3,2‐c]pyridine Derivatives.

et al. 2011

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A Convenient Approach to the Synthesis of Furo-and Thieno-[3,2-c]pyridine Derivatives. -Condensation of dihydrofuran-and -thiophenecarbonitriles (I) and (V) possessing an active methylene group with N,N-dimethylformamide dimethyl acetal (II) results in the formation of enamines (III) and (VI). Subsequent treatment of (III) and (VI) with ammonium acetate followed by exchange reactions of amines affect intramolecular cyclization leading to furo-and thienopyridines (IV) and (VII). Furo-and thienopyridinones (X) and (XII) are directly constructed from (VIII) and (XI) and amine (IX) in a one-pot process without isolation of the intermediate acetamide derivative. -(MARUOKA*, H.; OKABE, F.; YAMASAKI, K.; MASUMOTO, E.; FUJIOKA, T.; YAMAGATA, K.; Heterocycles 82 (2010) 1, 867-880, http://dx.doi.org/10.3987/com-10-s(e)47 ; Fac. Pharm. Sci., Fukuoka Univ.,

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A Convenient Approach to the Synthesis of Furo- and Thieno-[3,2-c]pyridine Derivatives

Cited by 6 publications

References 31 publications

[5C + 1N] Annulations: Two Novel Routes to Substituted Dihydrofuro[3,2-c]pyridines

[5C + 1N] Annulations: Two Novel Routes to Substituted Dihydrofuro[3,2-c]pyridines

Brønsted Acid‐Promoted Cascade Alkylation/Cyclization of Pyrroles with N,N‐Dimethylaminomethyleneglutaconic Acid Dinitrile: A Concise Route to Cyclopenta[b]pyrroles

ChemInform Abstract: A Convenient Approach to the Synthesis of Furo‐ and Thieno‐[3,2‐c]pyridine Derivatives.

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