Abstract
Reactions of 3-[(N-aryl-N-chloroacetyl)amino]-2-formylindoles with substituted anilines gave 1,4-diaryl-2-oxo-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indol-4-ium chlorides and those with 4-aminopyridine yielded 4-amino-1-(1-aryl-2-oxo-2,5-dihydro-1H-pyrido[3,2-b]indol-3-yl)pyridinium chlorides. Reduction of 1,2,3,6-tetrahydrodiazepinoindol-4-ium chlorides afforded the corresponding hexahydro derivatives. An alternative synthesis of 1-(4-nitrophenyl)-3-oxo-4-phenyl-1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole from 3-[N-(4-nitrophenyl)amino]-2-[(phenylimino)methyl]indole was developed. The method involves the following sequence of transformations: reduction, chloroacetylation, and intramolecular alkylation.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
M. D. Mashkovskii, Lekarstvennye sredstva [Drugs], 14th ed., Novaya Volna, Khar’kov, 2000, 1, 540 pp.; 2, 608 pp. (in Russian).
V. G. Granik, Lekarstva. Farmakologicheskii, biokhimicheskii i khimicheskii aspekty [Drugs. Pharmacological, Biochemical, and Chemical Aspects], Vuzovskaya Kniga, Moscow, 2001, p. 406 (in Russian).
US Pat. 3_736_324; Chem. Abstr., 1973, 79, 32118s.
F. Gatta, V. Zaccari, J. P. Huidolbro-Toro, and S. Chiavarelli, Farmaco, Ed. Sci., 1975, 10, 8.
US Pat. 3 689 503; Chem. Abstr., 1972, 77, 152241y.
N. A. Lantsetti, S. Yu. Ryabova, L. M. Alekseeva, A. S. Shashkov, and V. G. Granik, Izv. Akad. Nauk, Ser. Khim., 2002, 470 [Russ. Chem. Bull., Int. Ed., 2002, 51, 506].
S. Yu. Ryabova, N. A. Rastorgueva, E. A. Lisitsa, L. M. Alekseeva, and V. G. Granik, Izv. Akad. Nauk, Ser. Khim., 2003, 1312 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1386].
J. Tennant, Comprehensive Organic Chemistry, Eds D. Barton and W. D. Ollis, Pergamon Press, Oxford-New York-Toronto-Sidney-Paris-Frankfurt, 1979.
J. G. Cannon, Pharmacology for Chemists, Oxford University Press, New York-Oxford, 1999, 272 pp.
The Merck Index, 13th ed., Merck and Co. Inc., Whitehouse Station, New York, 2001, 3963.
N. A. Rastorgueva, S. Yu. Ryabova, E. A. Lisitsa, L. M. Alekseeva, and V. G. Granik, Izv. Akad. Nauk, Ser. Khim., 2003, 2036 [Russ. Chem. Bull., Int. Ed., 2003, 52, 2149].
R. Cumin, E. F. Bandle, E. Gamzu, and W. E. Haefely, Psychopharmacology (Berl.), 1982, 78, 104.
S. Yu. Ryabova, N. Z. Tugusheva, L. M. Alekseeva, and V. G. Granik, Khim.-Farm. Zh., 1996, 30, 7, 42 [Pharm. Chem. J., Int. Ed., 1996, 30, 7, 472 (Engl. Transl.)].
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2193–2199, December, 2006.
Rights and permissions
About this article
Cite this article
Ryabova, S.Y., Alekseeva, L.M., Rastorgueva, N.A. et al. A new method for the synthesis of [1,4]diazepino[6,5-b]indole derivatives. Russ Chem Bull 55, 2278–2284 (2006). https://doi.org/10.1007/s11172-006-0583-6
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-006-0583-6