Fine tuning the outcome of 1, 3-dipolar cycloaddition reactions of benzimidazolium ylides to activated alkynes. Issue 19 (12th May 2016)

• Record Type: Journal Article
• Authors: Georgescu, Emilian; Nicolescu, Alina; Georgescu, Florentina; Teodorescu, Florina; Shova, Sergiu; Marinoiu, Adriana T.; Dumitrascu, Florea; Deleanu, Calin
• Is Part Of: Tetrahedron. Volume 72:Issue 19(2016)
• Page Start: 2507
• Page End: 2520
• Publication Date: 2016-05-12
• Subjects: Nitrogen heterocycles -- Pyrrolo[1, 2-a]quinoxaline -- Pyrrolo[1, 2-a]benzimidazole -- Ylides -- Cycloaddition; LJLMNZZHESVPMP-UHFFFAOYSA-N -- GKKKVMZMGYUCTI-UHFFFAOYSA-M -- AEBCFEONCJXCPW-UHFFFAOYSA-N -- XULSQNWVYYHXMR-UHFFFAOYSA-M -- NDGUTFZEZCWWRG-UHFFFAOYSA-N -- XLBSUTDMDYZXBO-UHFFFAOYSA-N -- XRUYIPIPQUEPPX-UHFFFAOYSA-M -- ZTUNCVKZYSWEEQ-UHFFFAOYSA-N -- JFPHOFBLYWUGHX-UHFFFAOYSA-N -- VOYCWQNEPJSSTP-UHFFFAOYSA-N -- SIMPNGFZNWBGHP-UHFFFAOYSA-M -- IXODYOPVCKSGJW-UHFFFAOYSA-N -- IRLMESSHOSNXLQ-UHFFFAOYSA-M -- AQGLOJXIQWKJAT-UHFFFAOYSA-N -- RRGMHLZCKKOKDQ-UHFFFAOYSA-N -- PSSCWIOLANYDLJ-UHFFFAOYSA-N -- OWNOYSJXTSCKLV-UHFFFAOYSA-M -- GRSPGVZLWWFRES-UHFFFAOYSA-N -- NILFSKXQUJDUDQ-UHFFFAOYSA-N -- HBWKXTJPQQNTBY-UHFFFAOYSA-M -- UNXDMWOCNNWFJT-UHFFFAOYSA-N -- ZSAZXBZVMWZBPT-UHFFFAOYSA-N -- MSOTUYPNIDQITC-UHFFFAOYSA-M -- UKISEIZCGVDEMP-UHFFFAOYSA-N -- DGGXXAVFVPRIAS-UHFFFAOYSA-N -- XYIUKRXCOAXINA-UHFFFAOYSA-M -- PTWOBWMRYHZWJD-UHFFFAOYSA-N -- BVEQNSZZGHGTSY-UHFFFAOYSA-N -- BVUYDXAVRKAPKR-UHFFFAOYSA-N -- DFAZRKFUWAOHNT-UHFFFAOYSA-N -- FPOQGUZWSKUMSF-UHFFFAOYSA-N -- DHMOTQZITOMCRJ-UHFFFAOYSA-M -- AOXUEPKUCDYVCB-UHFFFAOYSA-N -- YFCSWGVGAHDISP-UHFFFAOYSA-M -- AKQNRIZIELCRNX-UHFFFAOYSA-N -- KDUACWLFJRJKPF-UHFFFAOYSA-N -- WIVXBLVWCFOZQY-UHFFFAOYSA-N -- CPLFHJUOKFSPLR-UHFFFAOYSA-M -- KHTXMGDMOFAFEB-UHFFFAOYSA-N -- JSWXCJJVMXYABI-UHFFFAOYSA-N -- QOKYXOAHCGMQNC-UHFFFAOYSA-M -- DKRVTVDNBGKDMF-UHFFFAOYSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.03.086
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 1, 3-Dipolar cycloaddition reactions of benzimidazolium ylides, generated from 3-phenacylbenzimidazolium bromides, to non-symmetrical activated dipolarophiles in various reaction conditions led to complex mixtures of pyrrolo[1, 2- a ]benzimidazole and pyrrolo[1, 2- a ]quinoxaline derivatives. In order to explain all experimental results, the influence of reaction conditions on the reaction products was investigated. For the first time, 4-hydroxy-4, 5-dihydropyrrolo[1, 2- a ]quinoxaline derivatives6, pyrrolo[1, 2- a ]quinoxalinium quaternary salts8, as well as 4-methoxy-4, 5-dihydropyrrolo[1, 2- a ]quinoxalines9, were separated, fully characterized and their interconversions are presented, together with a proposed reaction mechanism. Graphical abstract: