The reaction of 3-NHR-isoquinolin-1(2H)-ones (R = Ar) with aromatic aldehydes in the presence of Me3SiCl or in acetic acid leads to the formation of derivatives of dibenzo[b,f][1, 8]naphthyridin-5(6H)- one and benzo[f]isoquino[3,4-b][1, 8]naphthyridine-5,9(6H,7H)-dione. The reaction for R = Het in the presence of Me3SiCl gives derivatives of 5H-pyrido[1',2':1,2]pyrimido[4,5-c]isoquinolin-5-one, benzo[f]isoquinoline[3,4-b][1,8]naphthyridine-5,9[6H,7H]-dione, and derivatives of new heterocyclic systems, 5H-pyrazino[1',2':1,2]pyrimido[4,5-c]isoquinolin-5-one, 5H-[1,3]thiazolo[3',2':1,2]pyrimido- [4,5-c]isoquinolin-5-one, 5-H-benzo[f]pyrazolo[3,4-b][1,8]naphthyridin-5-one, and isoquino[3,4-b]- [1,5]naphthyridin-5(6H)-one. The effect of the structure of substituent R and nature of the substituent in the benzaldehydes on the structure of the reaction products was studied.
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For Communication 36, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 417–431, March, 2011.
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Potikha, L.M., Gutsul, R.M., Plaskon, A.S. et al. Condensed isoquinolines. 37.* Heterocyclization using 3-(arylamino)- and 3-(hetarylamino)isoquinolin-1(2H)-ones. Chem Heterocycl Comp 47, 342–354 (2011). https://doi.org/10.1007/s10593-011-0763-7
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DOI: https://doi.org/10.1007/s10593-011-0763-7
Keywords
- 3-aminoisocarbostyryl
- benzo[f]isoquino[3,4-b][1,8]naphthyridine
- benzo[f]pyrazolo[3,4-b]- [1,8]naphthyridine
- dibenzo[b,f][1,8]naphthyridine
- isoquino[3,4-b][1,5]naphthyridine
- pyrazino[1',2':1,2]- pyrimido[4,5-c]isoquinoline
- pyrido[1',2':1,2]pyrimido[4,5-c]isoquinoline
- [1,3]thiazolo[3',2':1,2]pyrimido- [4,5-c]isoquinoline