A Straightforward Synthesis
of 2-(1-Vinyl-1H-pyrrol-2-yl)-1H-benzimidazoles from 1-Vinyl-1H-pyrrole-2-carbaldehydes and o-Phenylenediamine

Boris A. Trofimov; Andrei V. Ivanov; Elena V. Skital’tseva; Alexander M. Vasil’tsov; Igor A. Ushakov; Konstantin B. Petrushenko; Al’bina I. Mikhaleva

doi:10.1055/s-0029-1216996

PAPER

A Straightforward Synthesis of 2-(1-Vinyl-1H-pyrrol-2-yl)-1H-benzimidazoles from 1-Vinyl-1H-pyrrole-2-carbaldehydes and o-Phenylenediamine

Boris A. Trofimov*, Andrei V. Ivanov, Elena V. Skital’tseva, Alexander M. Vasil’tsov, Igor A. Ushakov, Konstantin B. Petrushenko, Al’bina I. Mikhaleva
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation
Fax: +7(3952)419346; e-Mail: boris_trofimov@irioch.irk.ru;

Abstract

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Abstract

Hitherto inaccessible 1-vinylpyrrole-benzimidazole ensembles have been synthesized by the condensation of 1-vinyl-1H-pyrrole-2-carbaldehydes with o-phenylenediamine either directly or via the intermediate Schiff bases of the 1-vinyl-1H-pyrrole-2-carbaldehydes (1% TFA, DMSO, air atmosphere, 60-70 ˚C, 1 h) in yields up to 89%, the intermediate Schiff bases of exclusively E configuration being isolated in 91-98% yield (1% TFA, DMSO, r.t., 30 min). The synthesized 2-(1-vinyl-1H-pyrrol-2-yl)-1H-benzimidazoles are intensely fluorescent, covering the practically important blue region (λ_max 343-417 nm, Stokes shift 31-91 nm).

Key words

1-vinyl-1H-pyrrole-2-carbaldehydes - pyrrolylbenzimidazoles - o-phenylenediamine - Schiff bases - oxidative condensation

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References

<A NAME="RZ12809SS-1A">1a</A> Dykstra CC, Perfect J, Boykin DW, Wilson WD, and Tidwell RR. inventors; US Patent 5639755. ; Chem. Abstr. 1997, 126, 131457x

<A NAME="RZ12809SS-1B">1b</A> Dykstra CC, Boykin D, and Tidwell RR. inventors; PCT Int. Appl. WO 98 38 170. ; Chem. Abstr. 1998, 129, 230727d

<A NAME="RZ12809SS-1C">1c</A> Renneberg D. Dervan PB. J. Am. Chem. Soc. 2003, 125: 5707

<A NAME="RZ12809SS-1D">1d</A> Viger A. Dervan PB. Bioorg. Med. Chem. 2006, 14: 8539

<A NAME="RZ12809SS-1E">1e</A> Starčević K. Kralj M. Ester K. Sabol I. Grce M. Pavelić K. Karminski-Zamola G. Bioorg. Med. Chem. 2007, 15: 4419

<A NAME="RZ12809SS-2">2</A> Batista RMF. Costa SPG. Belsley M. Raposo MM. Tetrahedron 2007, 63: 9842

<A NAME="RZ12809SS-3">3</A> Haugland RP, and Kang HC. inventors; (Molecular Probes, Inc.) US Patent 5248782. ; Chem. Abstr. 1994, 120, 32877d

<A NAME="RZ12809SS-4A">4a</A> El’chaninov MM. Simonov AM. Oleinikova LYa. Chem. Heterocycl. Compd. (Engl. Transl.) 1980, 16: 59

<A NAME="RZ12809SS-4B">4b</A> Jones RA. Quintanilla-Lopez G. Taheri SAN. Hania MM. Öztürk O. Zuilhof H. ARKIVOC 2000, (iii): 382

<A NAME="RZ12809SS-4C">4c</A> Lin S. Yang L. Tetrahedron Lett. 2005, 46: 4315

<A NAME="RZ12809SS-4D">4d</A> Chakrabarty M. Mukherji A. Mukherjee R. Arima S. Harigaya Y. Tetrahedron Lett. 2007, 48: 5239

<A NAME="RZ12809SS-4E">4e</A> Du L.-H. Wang Y.-G. Synthesis 2007, 675

<A NAME="RZ12809SS-5">5</A> Szydlo F. Andrioletti B. Rose E. Duhayon C. Tetrahedron Lett. 2008, 49: 3749

<A NAME="RZ12809SS-6">6</A> De Selms RC. J. Org. Chem. 1962, 27: 2163

<A NAME="RZ12809SS-7">7</A> George B. Papadopoulos EP. J. Org. Chem. 1977, 42: 441

<A NAME="RZ12809SS-8">8</A> Yang D. Fokas D. Li J. Yu L. Baldino CM. Yang D. Fokas D. Li J. Yu L. Baldino CM. Synthesis 2005, 47

<A NAME="RZ12809SS-9A">9a</A> Tedeschi RJ. Encyclopedia of Physical Science and Technology Vol. 1: Academic Press; San Diego: 1992. p.27

<A NAME="RZ12809SS-9B">9b</A> Gonzalez F. Sanz-Cervera JF. Williams RM. Tetrahedron Lett. 1999, 40: 9

<A NAME="RZ12809SS-9C">9c</A> Abele E. Lucevics E. Chem. Heterocycl. Compd. (Engl. Transl.) 2001, 37: 141

<A NAME="RZ12809SS-9D">9d</A> Trofimov BA. In The Chemistry of Heterocyclic Compounds Vol. 48: Jones RA. Wiley & Sons; New York: 1992. p.131

<A NAME="RZ12809SS-10">10</A> Trofimov BA. Mikhaleva AI. Vasil’ev AN. Lopyrev VA. Titova IA. Bzhezovskii VM. Sigalov MV. Khim. Geterotsikl. Soedin. 1981, 1422 ; Chem. Abstr. 1982, 96, 199581

<A NAME="RZ12809SS-11A">11a</A> Mikhaleva AI. Zaitsev AB. Ivanov AV. Schmidt EYu. Vasil’tsov AM. Trofimov BA. Tetrahedron Lett. 2006, 47: 3693

<A NAME="RZ12809SS-11B">11b</A> Mikhaleva AI. Ivanov AV. Skital’tseva EV. Ushakov IA. Vasil’tsov AM. Trofimov BA. Synthesis 2009, 587

<A NAME="RZ12809SS-12">12</A> Vasil’tsov AM. Ivanov AV. Ushakov IA. Mikhaleva AI. Trofimov BA. Synthesis 2007, 452

<A NAME="RZ12809SS-13A">13a</A> Trofimov BA. Mikhaleva AI. Morozova LV. Vasil’ev AN. Sigalov MV. Khim. Geterotsikl. Soedin. 1983, 269 ; Chem. Abstr. 1983, 98, 215442

<A NAME="RZ12809SS-13B">13b</A> Trofimov BA. Morozova LV. Sigalov MV. Mikhaleva AI. Markova MV. Makromol. Chem. 1987, 188: 2251

<A NAME="RZ12809SS-13C">13c</A> Trofimov BA. Markova MV. Morozova LV. Mikhaleva AI. ARKIVOC 2001, (ix): 24

<A NAME="RZ12809SS-14">14</A> Mikhaleva AI. Ivanov AV. Vasil’tsov AM. Ushakov IA. Ma JS. Yang G. Chem. Heterocycl. Compd. (Engl. Transl.) 2008, 44: 1117

<A NAME="RZ12809SS-15A">15a</A> Wu Z. Chen Q. Xiong S. Xin B. Zhao Z. Jiang L. Ma JS. Angew. Chem. 2003, 115: 3393

<A NAME="RZ12809SS-15B">15b</A> Wu Z. Chen Q. Yang G. Xiao C. Liu J. Yang S. Ma JS. Sens. Actuators, B 2004, 99: 511

<A NAME="RZ12809SS-15C">15c</A> Yang L. Shan X. Chen Q. Wang Z. Ma JS. Eur. J. Inorg. Chem. 2004, 1474

<A NAME="RZ12809SS-15D">15d</A> Zhang G. Yang G. Ma JS. In New Developments in Organometallic Chemistry Research Cato MA. Nova Science Publishers; New York: 2006. p.63

<A NAME="RZ12809SS-16">16</A> Omura K. Swern D. Tetrahedron 1978, 34: 1651

<A NAME="RZ12809SS-17">17</A> Petrushenko IK. Smirnov VI. Petrushenko KB. Schmidt EYu. Zorina NV. Rusakov YuYu. Vasil’tsov AM. Mikhaleva AI. Trofimov BA. Russ. J. Gen. Chem. (Engl. Transl.) 2007, 77: 1386

<A NAME="RZ12809SS-18">18</A> Vasil’tsov AM. Schmidt EYu. Mikhaleva AI. Zorina NV. Zaitsev AB. Petrova OV. Krivdin LB. Petrushenko KB. Ushakov IA. Pozo-Conzalo C. Pomposo JA. Grande H.-J. Tetrahedron 2005, 61: 7756