An I 2 -mediated cascade reaction of 2'-bromoacetophenones with benzohydrazides/benzamides leading to quinazolino[3,2-b]cinnoline or tryptanthrin derivatives

An efficient and facile protocol for the synthesis of quinazolinone-fused tetracyclic compounds through an iodine-mediated one-pot cascade reaction of 2'-bromoacetophenones with 2-aminobenzohydrazides or 2-aminobenzamides is reported. With 2-aminobenzohydrazides as the substrates, the reaction...

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Veröffentlicht in:Organic & biomolecular chemistry 2017-02, Vol.15 (6), p.1521-1529
Hauptverfasser: Guo, Shenghai, Zhai, Jianhui, Fan, Xuesen
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creator Guo, Shenghai
Zhai, Jianhui
Fan, Xuesen
description An efficient and facile protocol for the synthesis of quinazolinone-fused tetracyclic compounds through an iodine-mediated one-pot cascade reaction of 2'-bromoacetophenones with 2-aminobenzohydrazides or 2-aminobenzamides is reported. With 2-aminobenzohydrazides as the substrates, the reaction gave 5H-quinazolino[3,2-b]cinnoline-7,13-diones in moderate to good yields under metal-catalyst-free conditions. With 2-aminobenzamides as the substrates and CuBr as the catalyst, on the other hand, it afforded tryptanthrin derivatives with good efficiency. Mechanistically, the formation of the tetracyclic systems is initiated by iodination and oxidation of 2'-bromoacetophenones followed by a cascade procedure consisting of cyclocondensation, aromatization and intramolecular cyclization of the in situ formed 2-bromoarylglyoxals with 2-aminobenzohydrazides or 2-aminobenzamides, respectively.
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With 2-aminobenzohydrazides as the substrates, the reaction gave 5H-quinazolino[3,2-b]cinnoline-7,13-diones in moderate to good yields under metal-catalyst-free conditions. With 2-aminobenzamides as the substrates and CuBr as the catalyst, on the other hand, it afforded tryptanthrin derivatives with good efficiency. Mechanistically, the formation of the tetracyclic systems is initiated by iodination and oxidation of 2'-bromoacetophenones followed by a cascade procedure consisting of cyclocondensation, aromatization and intramolecular cyclization of the in situ formed 2-bromoarylglyoxals with 2-aminobenzohydrazides or 2-aminobenzamides, respectively.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c6ob02699k</identifier><identifier>PMID: 28116380</identifier><language>eng</language><publisher>England</publisher><subject>Acetophenones - chemistry ; Benzamides - chemistry ; Heterocyclic Compounds, 2-Ring - chemical synthesis ; Heterocyclic Compounds, 2-Ring - chemistry ; Hydrazines - chemistry ; Iodine - chemistry ; Molecular Structure ; Quinazolines - chemical synthesis ; Quinazolines - chemistry</subject><ispartof>Organic &amp; biomolecular chemistry, 2017-02, Vol.15 (6), p.1521-1529</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c184t-e7693662bf4303a87bd6fd52bdaac52a83d53d23676736922355264f237c9a393</citedby><cites>FETCH-LOGICAL-c184t-e7693662bf4303a87bd6fd52bdaac52a83d53d23676736922355264f237c9a393</cites><orcidid>0000-0002-2797-4281 ; 0000-0002-2040-6919</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28116380$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Guo, Shenghai</creatorcontrib><creatorcontrib>Zhai, Jianhui</creatorcontrib><creatorcontrib>Fan, Xuesen</creatorcontrib><title>An I 2 -mediated cascade reaction of 2'-bromoacetophenones with benzohydrazides/benzamides leading to quinazolino[3,2-b]cinnoline or tryptanthrin derivatives</title><title>Organic &amp; biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>An efficient and facile protocol for the synthesis of quinazolinone-fused tetracyclic compounds through an iodine-mediated one-pot cascade reaction of 2'-bromoacetophenones with 2-aminobenzohydrazides or 2-aminobenzamides is reported. 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source MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Acetophenones - chemistry
Benzamides - chemistry
Heterocyclic Compounds, 2-Ring - chemical synthesis
Heterocyclic Compounds, 2-Ring - chemistry
Hydrazines - chemistry
Iodine - chemistry
Molecular Structure
Quinazolines - chemical synthesis
Quinazolines - chemistry
title An I 2 -mediated cascade reaction of 2'-bromoacetophenones with benzohydrazides/benzamides leading to quinazolino[3,2-b]cinnoline or tryptanthrin derivatives
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