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Synthesis 2004(3): 373-376
DOI: 10.1055/s-2004-815950
DOI: 10.1055/s-2004-815950
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Facile Route to Pyrrolo[3′,4′:3,4]pyrido[1,2-a]benzimidazoles, Novel Heterocyclic Derivatives
Further Information
Received
3 August 2003
Publication Date:
03 February 2004 (online)
Publication History
Publication Date:
03 February 2004 (online)
Abstract
The title system derivatives were prepared in two steps. Thus the condensation of 2-benzimidazoleacetonitrile with ethyl 4-chloro-3-oxobutanoate led to the 3-chloromethyl-1,5-dihydro-1-oxopyrido[1,2-a]benzimidazole-4-carbonitrile. Further amination of the obtained chloronitrile with primary amines yielded 1-amino-2,3-dihydro-2-R-5H-pyrrolo[3′,4′:3,4]pyrido[1,2-a]benzimidazol-5-ones.
Key words
alkylations - 2-benzimidazoleacetonitrile - heterocycles - pyrrolo[3′,4′:3,4]pyrido[1,2-a]benzimidazoles - ring closure
-
1a
Gewald K.Hentschel M. J. Prakt. Chem. 1976, 318: 663 -
1b
Dave CG.Shah RR.Upadhyaya SP. J. Indian Chem. Soc. 1987, 64: 713 -
1c
Chen YL.Mansbach RS.Winter SM.Brooks E.Collins J.Corman ML.Dunaiskis AR.Faraci WS.Gallaschun RJ.Schmidt A.Schultz DW. J. Med. Chem. 1997, 40: 1749 -
1d
Teuber HJ.Schuetz G.Erkenbrecher E. Arch. Pharm. 1980, 313: 851 -
2a
Boosen KJ. Helv. Chim. Acta 1977, 60: 1256 -
2b
Pfister J,Weisenfeldt M, andEtzbach KH. inventors; Ger. DE 3902216. ; Chem. Abstr. 1990, 113, 10859 -
2c
Kovtunenko VA.Kupchevskaya IP.Tolmacheva VS.Kisel VM.Volovenko Yu. M. Ukr. Khim. Zh. 1995, 61: 43 ; Chem. Abstr. 1996, 124, 260965 -
2d
Volovenko YM.Shokol TV.Merkulov AS.Babichev FS. Ukr. Khim. Zh. (Russ. Ed.) 1993, 59: 55 ; Chem. Abstr. 1993, 119, 160185 -
2e
Volovenko YM.Tverdokhlebov AV.Gorulya AP.Shishkina SV.Zubatyuk RI.Shishkin OV. Eur. J. Org. Chem. 2002, 663 -
2f
Volovenko YM.Resnyanska EV.Tverdokhlebov AV. Collect. Czech. Chem. Commun. 2002, 67: 365 -
2g
Volovenko YM.Volovnenko TA.Tverdokhlebov AV.Ryabokon IG. Russ. J. Org. Chem. 2001, 37: 1323 -
2h
Tverdokhlebov AV.Volovenko YM.Shokol TV. Chem. Heterocycl. Compd. (Engl. Transl.) 1998, 34: 44 -
2i
Volovenko YM.Resnyanskaya EV.Tverdokhlebov AV. Chem. Heterocycl. Compd. (Engl. Transl.) 2002, 38: 324 -
3a
Babichev FS.Tyltin AK. Ukr. Khim. Zh. (Russ. Ed.) 1970, 36: 62 ; Chem. Abstr. 1970, 72, 132428 -
3b
Babichev FS.Tyltin AK.Shevchuk LI. Ukr. Khim. Zh. (Russ. Ed.) 1971, 37: 916 ; Chem. Abstr. 1972, 76, 153482 -
3c
Babichev FS.Tyltin AK.Shevchuk LI. Ukr. Khim. Zh. (Russ. Ed.) 1973, 39: 348 ; Chem. Abstr. 1973, 79, 66289 -
3d
Babichev FS.Briks YL.Romanov NN. Ukr. Khim. Zh. (Russ. Ed.) 1981, 47: 291 ; Chem. Abstr. 1981, 94, 210275 -
3e
Kovtunenko VA.Falkovskaya OT.Tyltin AK.Babichev FS. Ukr. Khim. Zh. (Russ. Ed.) 1984, 50: 530 ; Chem. Abstr. 1985, 102, 220686 -
3f
Babichev FS.Briks YL.Romanov NN. Ukr. Khim. Zh. (Russ. Ed.) 1985, 51: 94 ; Chem. Abstr. 1985, 102, 220805 -
3g
Christiaens L.Renson M. Bull. Soc. Chim. Belg. 1972, 81: 609 -
3h
Christiaens L.Renson M. Tetrahedron 1972, 28: 5405 -
4a
Volovenko YM.Litvinenko SV.Babichev FS. Dokl. Akad. Nauk Ukr. SSR, Ser. B. 1988, 9: 32 ; Chem. Abstr. 1989, 111, 232735 -
4b
Kozynchenko AP.Volovenko YM.Promonenkov VK.Turov AV.Babichev FS. Khim. Geterotsikl. Soedin. 1988, 1119 ; Chem. Abstr. 1989, 110, 192771 -
4c
Volovenko YM.Litvinenko SV.Tabeleva TV.Babichev FS. Dokl. Akad. Nauk Ukr. SSR, Ser. B. 1989, 6: 33 ; Chem. Abstr. 1990, 112, 55781 -
4d
Kozynchenko AP.Volovenko YM.Babichev FS.Promonenkov VK. Ukr. Khim. Zh. (Russ. Ed.) 1989, 55: 737 ; Chem. Abstr. 1990, 112, 77117 -
5a
Makarov VA.Tafeenko VA.Granik VG. Chem. Heterocycl. Compd. (Engl. Transl.) 1998, 34: 1423 -
5b
Passarotti CM.Valenti M.Marini M. Boll. Chim. Farm. 1995, 134: 639 -
5c
Mojtahedi MM.Saidi MR.Shizzi MS.Bolourtchian M. Synth. Commun. 2002, 32: 851 -
5d
Reiter J.Pongo L.Somorai T.Pallagi I. Monatsh. Chem. 1990, 121: 173 -
5e
Okabe T,Mukai K, andHirano M. inventors; Ger. DE 3003337. ; Chem. Abstr. 1981, 94, 121710 -
6a
Rangnekar DW.Rajadhyaksha DD. Indian J. Technol. 1990, 28: 75 ; Chem. Abstr. 1990, 113, 134153 -
6b
Rida SM.Soliman FSG.Badawey ESAM.Kappe T. J. Heterocycl. Chem. 1988, 25: 1725 -
7a
Rimoli MG.Avallone L.De Caprariis P.Luraschi E.Abignente E.Filippelli W.Berrino L.Rossi F. Eur. J. Med. Chem. 1997, 32: 195 -
7b
Palagiano F.Arenare L.Luraschi E.De Caprariis P.Grandolini G.Ambrogi V.Perioli L.Filippelli W.Falcone G.Rossi F. Farmaco 1996, 51: 483 -
7c
Palagiano F.Arenare L.Luraschi E.De Caprariis P.Abignente E.D’Amico M.Filippelli W.Rossi F. Eur. J. Med. Chem. 1995, 30: 901 - 8
Gokhale UV.Seshadri S. Dyes Pigments 1987, 8: 157