Summary
The reaction betweeno-phenylenediamine and eighteen aromatic aldehydes under acidic conditions has been investigated, and found to yield mono-and disubstituted benziminazoles in varying proportions, and in two cases, a benzodiazacycloheptatriene derivative also. Thirteen new compounds obtained have been characterised. Stepwise mechanism for the formation of the different types of products is suggested, and the influence of substitutuents in the aldehydes on the mode of the reaction and cyclisation is discussed.
Similar content being viewed by others
References
Ladenburg and EngelbrechtBer., 1878,11, 1653.
— and RugheimerIbid.,, 1878,11, 1656.
HinsbergIbid.,, 1886,19, 2025;Ibid. Ber, 1887,20, 1585.
— and FunckeIbid.,, 1893,26, 3092;Ibid. Ber., 1894,27, 2187.
Pinnow and WiskottIbid.,, 1899,32, 905.
Weil and MarcinkowskaRoczniki. Chem., 1934,14, 1312;C.A., 1935,29, 6233.
Sevens and SmetsBull. Soc. Chim. Belges., 1948,57, 32;C.A., 1951,45, 568.
Rao and RatnamCurr. Sci., 1955,24, 299.
FischerBer., 1892,25, 2826;Ibid. Ber., 1893,26, 187.
BoydJ.C.S., 1894,65, 879.
Hinsberg and KollerBer., 1896,29, 1497.
Jacobson, Jaenicke and MeyerIbid.,, 1896,29, 2680.
Stephens and BowerJ.C.S., 1949, 2971;Ibid. J.C.S., 1950, 1722.
Jerchel, Fischer and Kracht,Ann., 1952,575, 162.
Dyson and StephensBrit., 669, 402, Apr. 2, 1952;C.A., 1953,47, 2215.
Chariton, Maliphant, Oxley and PeakJ.C.S., 1951, 485.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Rao, N.V.S., Ratnam, C.V. Studies in the formation of heterocyclic rings containing nitrogen. Proc. Indian Acad. Sci. 43, 173–180 (1956). https://doi.org/10.1007/BF03052777
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF03052777