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Synthesis of 11H-4b,10b-dihydro[1]benzopyrano[4,3-c]isoquinoline-6,11(5H)-diones and 13H-6c,12b-dihydronaphtho[1′,2′:5,6]-pyrano[4-3c]isoquinoline-8,13(7H)-dione from homophthalic anhydride and N-(2-hydroxyarylidene)alkylamines

(1994) TETRAHEDRON. 50(31). p.9399-9410
Author
Organization
Abstract
2-Alkyl-3-(2-hydroxyaryl)-3,4-dihydro-1(2H)-isoquinolinone-4-carboxylic acids (5,13) were prepared from homophthalic anhydride (1) and N-(2-hydroxyarylidene)alkylamines (2,10). The acids 5,13 showed a tendency towards cyclodehydration to give isoquinoline derivatives with fused [1]benzopyrane (8) or naphthopyrane (12) ring system. The relative configurations of the novel fused heterocyclic compounds 5,8,12,13 and related compounds were determined by NMR studies, and in the case of 13 also by means of X-ray analysis. Some MM2 force field molecular mechanics calculations on some selected fused heterocycles were executed. The naphtho[1',2':5,6]pyrano[4,3-c]-isoquinoline ring system incorporated in the lactone 12 is hitherto unreported.
Keywords
CONDENSATION

Citation

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Chicago
Georgieva, Angelina, Elena Stanoeva, Katya Karamfilova, Stefan Spassov, Olyana Angelova, Marietta Haimova, Norbert De Kimpe, and Mark Boelens. 1994. “Synthesis of 11H-4b,10b-dihydro[1]benzopyrano[4,3-c]isoquinoline-6,11(5H)-diones and 13H-6c,12b-dihydronaphtho[1′,2′:5,6]-pyrano[4-3c]isoquinoline-8,13(7H)-dione from Homophthalic Anhydride and N-(2-hydroxyarylidene)alkylamines.” Tetrahedron 50 (31): 9399–9410.
APA
Georgieva, Angelina, Stanoeva, E., Karamfilova, K., Spassov, S., Angelova, O., Haimova, M., De Kimpe, N., et al. (1994). Synthesis of 11H-4b,10b-dihydro[1]benzopyrano[4,3-c]isoquinoline-6,11(5H)-diones and 13H-6c,12b-dihydronaphtho[1′,2′:5,6]-pyrano[4-3c]isoquinoline-8,13(7H)-dione from homophthalic anhydride and N-(2-hydroxyarylidene)alkylamines. TETRAHEDRON, 50(31), 9399–9410.
Vancouver
1.
Georgieva A, Stanoeva E, Karamfilova K, Spassov S, Angelova O, Haimova M, et al. Synthesis of 11H-4b,10b-dihydro[1]benzopyrano[4,3-c]isoquinoline-6,11(5H)-diones and 13H-6c,12b-dihydronaphtho[1′,2′:5,6]-pyrano[4-3c]isoquinoline-8,13(7H)-dione from homophthalic anhydride and N-(2-hydroxyarylidene)alkylamines. TETRAHEDRON. 1994;50(31):9399–410.
MLA
Georgieva, Angelina, Elena Stanoeva, Katya Karamfilova, et al. “Synthesis of 11H-4b,10b-dihydro[1]benzopyrano[4,3-c]isoquinoline-6,11(5H)-diones and 13H-6c,12b-dihydronaphtho[1′,2′:5,6]-pyrano[4-3c]isoquinoline-8,13(7H)-dione from Homophthalic Anhydride and N-(2-hydroxyarylidene)alkylamines.” TETRAHEDRON 50.31 (1994): 9399–9410. Print.
@article{198917,
  abstract     = {2-Alkyl-3-(2-hydroxyaryl)-3,4-dihydro-1(2H)-isoquinolinone-4-carboxylic acids (5,13) were prepared from homophthalic anhydride (1) and N-(2-hydroxyarylidene)alkylamines (2,10). The acids 5,13 showed a tendency towards cyclodehydration to give isoquinoline derivatives with fused [1]benzopyrane (8) or naphthopyrane (12) ring system. The relative configurations of the novel fused heterocyclic compounds 5,8,12,13 and related compounds were determined by NMR studies, and in the case of 13 also by means of X-ray analysis. Some MM2 force field molecular mechanics calculations on some selected fused heterocycles were executed. The naphtho[1',2':5,6]pyrano[4,3-c]-isoquinoline ring system incorporated in the lactone 12 is hitherto unreported.},
  author       = {Georgieva, Angelina and Stanoeva, Elena and Karamfilova, Katya and Spassov, Stefan and Angelova, Olyana and Haimova, Marietta and De Kimpe, Norbert and Boelens, Mark},
  issn         = {0040-4020},
  journal      = {TETRAHEDRON},
  keyword      = {CONDENSATION},
  language     = {eng},
  number       = {31},
  pages        = {9399--9410},
  title        = {Synthesis of 11H-4b,10b-dihydro[1]benzopyrano[4,3-c]isoquinoline-6,11(5H)-diones and 13H-6c,12b-dihydronaphtho[1{\textquotesingle},2{\textquotesingle}:5,6]-pyrano[4-3c]isoquinoline-8,13(7H)-dione from homophthalic anhydride and N-(2-hydroxyarylidene)alkylamines},
  url          = {http://dx.doi.org/10.1016/S0040-4020(01)85515-0},
  volume       = {50},
  year         = {1994},
}

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