Abstract

Background: This paper showed the synthetic capability of the indolo[2,3-b]quinoxaline nucleus to be provided as an excellent precursor for the synthesis of various heterocyclic compounds. These synthetic routes proceed via the formation of 3-(6H-indolo[2,3-b]quinoxalin-6-yl) propane hydrazide (2). The carbohydrazide 2 and its reactions with different reagents give five and six-membered rings, such as 1,3,4-thiadiazole, 1,3,4- oxadiazole, 1,2,4-triazole, and 1,2,4-triazine.

Methods: All chemicals used in the current study were of analytical grade. Melting points were determined using an APP Digital ST 15 melting point apparatus and were uncorrected. FT-IR spectra were recorded on a Pye- Unicam SP3-100 and Shimadzu-408 spectrophotometers in KBr pellets and given in (cm^-1) KBr. The NMR spectra were detected by a Bruker AV-400 spectrometer (400 MHz for ¹H, 100 MHz for ¹³C and 40.55 MHz for ¹⁵N), Institute of Organic Chemistry, Karlsruhe, Germany. Chemical shifts were expressed as δ (ppm) with TMS as an internal reference. Mass spectrometry was provided on a Varian MAT 312 instrument in EI mode (70 eV).

Results: The target compounds were obtained, and their structures were completely elucidated by various spectral and elemental analyses (Ft-IR, ¹H-NMR, ¹³C-NMR, and mass spectrometry).

Conclusion: The current work showed a view of the reactivity of the carbohydrazide group. The carbohydrazide 2 was obtained from the hydrazinolysis of carboethoxy compound 1 and exploited as a key intermediate to synthesize heterocyclic compounds with different rings.

Keywords: Ethyl 3-chloropropionate, indolo[2, 3-b]quinoxaline, carbohydrazide, pyrazole, 1, 3, 4-thiadiazoles, 4-oxadiazoles, 2, 4- triazole.