New bis-spiropyranes on the base of dipyrrolonaphtho[1,4]diazepine and dipyrropolobenzoquinoqsaline

Author: marina trapaidze
Co-authors: Kvinikadze Sofiko
Keywords: dipyrrolonaphthodiazepine, Fishers baze, NMR-speqtra
Annotation:

New bis-spiropyrans on the base of dipyrrolonaphtho[1,4]diazepine and dipyrropolobenzoquinoxaline Marina Trapaidze marina.trapaidze@tsu.ge Department of Chemistry, The Faculty of Exact and Natural Sciences, Tbilisi State University, #3 Chavchavadze Ave. Tbilisi. In the present work is displayed the synthesis of dipyrrolonaphthodiazepine cycle containing new Fischer’s base’s bis analogs which was fulfilled via coupling of (2,3,3,8,8,9-hexamethyl-3,8-dihydrobenzo¬[e]pyrrolo¬[3,2-g]indole) with 1,3-dipropane. The treatment of obtained tertiary salt with alkali gave the appropriate Fischer’s base - (1,5,6,9-tetrahydro-1,1,9,9-tetramethyl-2,8-dimethylen-4H-dipyrrolo[1,2,3-e,f:3,2,1-n,o]naphtho[2,3-b][1,4]diazepine). The condensation of Fischer’s base bis analogs with 5-bromo salicylic aldehyde and 3-chloro-5-nitro-salicyclic aldehyde gave corresponding bis-spiropyrans - (bis(6-brom-2H-chromen-2-spiro)1,5,6,9-tetrahydro-1,1,9,9-tetramethyl-4H-dipyrrolo[1,2,3-e,f:3,2,1-n,o]naphtho¬[2,3-b][1,4]¬diazepine and (bis(6-nitro-8-chloro-2H-chromen-2-spiro)1,5,6,9-tetrahydro-1,1,9,9-tetramethyl-4H-dipyrrolo[1,2,3-e,f:3,2,1-n,o]naphtho[2,3-b][1,4]diazepine. The confirmation of synthesized new compounds’ structure is given by complete spectral analysis - 1H- and 13C-NMR and Mass spectra. 1H and 13C-NMR, Mass spectra of previously synthesized bis-spiropyrans on the base of dipyrrolobenzoquinoxalines are also considered. New bis-spiropyrans on the base of dipyrrolonaphtho[1,4]diazepine and dipyrropolobenzoquinoxaline Marina Trapaidze marina.trapaidze@tsu.ge Department of Chemistry, The Faculty of Exact and Natural Sciences, Tbilisi State University, #3 Chavchavadze Ave. Tbilisi. In the present work is displayed the synthesis of dipyrrolonaphthodiazepine cycle containing new Fischer’s base’s bis analogs which was fulfilled via coupling of (2,3,3,8,8,9-hexamethyl-3,8-dihydrobenzo¬[e]pyrrolo¬[3,2-g]indole) with 1,3-dipropane. The treatment of obtained tertiary salt with alkali gave the appropriate Fischer’s base - (1,5,6,9-tetrahydro-1,1,9,9-tetramethyl-2,8-dimethylen-4H-dipyrrolo[1,2,3-e,f:3,2,1-n,o]naphtho[2,3-b][1,4]diazepine). The condensation of Fischer’s base bis analogs with 5-bromo salicylic aldehyde and 3-chloro-5-nitro-salicyclic aldehyde gave corresponding bis-spiropyrans - (bis(6-brom-2H-chromen-2-spiro)1,5,6,9-tetrahydro-1,1,9,9-tetramethyl-4H-dipyrrolo[1,2,3-e,f:3,2,1-n,o]naphtho¬[2,3-b][1,4]¬diazepine and (bis(6-nitro-8-chloro-2H-chromen-2-spiro)1,5,6,9-tetrahydro-1,1,9,9-tetramethyl-4H-dipyrrolo[1,2,3-e,f:3,2,1-n,o]naphtho[2,3-b][1,4]diazepine. The confirmation of synthesized new compounds’ structure is given by complete spectral analysis - 1H- and 13C-NMR and Mass spectra. 1H and 13C-NMR, Mass spectra of previously synthesized bis-spiropyrans on the base of dipyrrolobenzoquinoxalines are also considered. In the present work is displayed the synthesis of dipyrrolonaphthodiazepine cycle containing new Fischer’s base’s bis analogs which was fulfilled via coupling of (2,3,3,8,8,9-hexamethyl-3,8-dihydrobenzo¬[e]pyrrolo¬[3,2-g]indole) with 1,3-dipropane. The treatment of obtained tertiary salt with alkali gave the appropriate Fischer’s base - (1,5,6,9-tetrahydro-1,1,9,9-tetramethyl-2,8-dimethylen-4H-dipyrrolo[1,2,3-e,f:3,2,1-n,o]naphtho[2,3-b][1,4]diazepine). The condensation of Fischer’s base bis analogs with 5-bromo salicylic aldehyde and 3-chloro-5-nitro-salicyclic aldehyde gave corresponding bis-spiropyrans - (bis(6-brom-2H-chromen-2-spiro)1,5,6,9-tetrahydro-1,1,9,9-tetramethyl-4H-dipyrrolo[1,2,3-e,f:3,2,1-n,o]naphtho¬[2,3-b][1,4]¬diazepine and (bis(6-nitro-8-chloro-2H-chromen-2-spiro)1,5,6,9-tetrahydro-1,1,9,9-tetramethyl-4H-dipyrrolo[1,2,3-e,f:3,2,1-n,o]naphtho[2,3-b][1,4]diazepine. The confirmation of synthesized new compounds’ structure is given by complete spectral analysis - 1H- and 13C-NMR and Mass spectra. 1H and 13C-NMR, Mass spectra of previously synthesized bis-spiropyrans on the base of dipyrrolobenzoquinoxalines are also considered.