Synthesis and reactions of 1-amino-1,5,6,10b-tetrahydroimidazo[2,1-a]isoquinolin-2(3H)-ones
- Author
- Joana Solovjova, Vytas Martynaitis, Wolfgang Holzer, Sven Mangelinckx (UGent) , Norbert De Kimpe (UGent) and Algirdas Šačkus
- Organization
- Abstract
- 1-Amino-1,5,6,10b-tetrahydroimidazo[2,1-a]isoquinolin-2(3H)-ones, as previously unknown ring-annelated isoquinolines with a 3-aminoimidazolidin-4-one scaffold, were selectively prepared upon reacting 2-carbamoylmethyl- or 2-ethoxycarbonylmethyl-3,4-dihydroisoquinolinium salts with hydrazine hydrate. Acylation of the primary amino group with benzoyl chlorides, followed by reductive ring cleavage of the annelated 4-imidazolidinone ring and final cyclodehydration of the N,N'-diacylhydrazines resulted in the synthesis of 1-methyl-2(5-aryl-[1,3,4]oxadiazol-2-ylmethyl)-1,2,3,4-tetrahydroisoquinolines which are of interest due to their potential use as bioisosteres of biologically active N-aryl-2-(1-methyl-3,4-dihydro-1H-isoquinolin-2-yl) acetamides.
- Keywords
- Ring annelation, isoquinolines, 1-amino-1, 5, 6, 10b-tetrahydroimidazo[2, 1-a]isoquinolin-2(3H)-ones, hydrazides, 1, 3, 4-oxadiazoles, ISOQUINOLINE ALKALOIDS, ASYMMETRIC-SYNTHESIS, BETA-PHENYLETHYLAMINES, DERIVATIVES, 2-AMINO-1, 3, 4-OXADIAZOLES, REARRANGEMENT, CONDENSATION, ACID
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-505622
- MLA
- Solovjova, Joana, et al. “Synthesis and Reactions of 1-Amino-1,5,6,10b-Tetrahydroimidazo[2,1-a]Isoquinolin-2(3H)-Ones.” ARKIVOC, no. 6, 2009, pp. 48–62, doi:10.3998/ark.5550190.0010.606.
- APA
- Solovjova, J., Martynaitis, V., Holzer, W., Mangelinckx, S., De Kimpe, N., & Šačkus, A. (2009). Synthesis and reactions of 1-amino-1,5,6,10b-tetrahydroimidazo[2,1-a]isoquinolin-2(3H)-ones. ARKIVOC, (6), 48–62. https://doi.org/10.3998/ark.5550190.0010.606
- Chicago author-date
- Solovjova, Joana, Vytas Martynaitis, Wolfgang Holzer, Sven Mangelinckx, Norbert De Kimpe, and Algirdas Šačkus. 2009. “Synthesis and Reactions of 1-Amino-1,5,6,10b-Tetrahydroimidazo[2,1-a]Isoquinolin-2(3H)-Ones.” ARKIVOC, no. 6: 48–62. https://doi.org/10.3998/ark.5550190.0010.606.
- Chicago author-date (all authors)
- Solovjova, Joana, Vytas Martynaitis, Wolfgang Holzer, Sven Mangelinckx, Norbert De Kimpe, and Algirdas Šačkus. 2009. “Synthesis and Reactions of 1-Amino-1,5,6,10b-Tetrahydroimidazo[2,1-a]Isoquinolin-2(3H)-Ones.” ARKIVOC (6): 48–62. doi:10.3998/ark.5550190.0010.606.
- Vancouver
- 1.Solovjova J, Martynaitis V, Holzer W, Mangelinckx S, De Kimpe N, Šačkus A. Synthesis and reactions of 1-amino-1,5,6,10b-tetrahydroimidazo[2,1-a]isoquinolin-2(3H)-ones. ARKIVOC. 2009;(6):48–62.
- IEEE
- [1]J. Solovjova, V. Martynaitis, W. Holzer, S. Mangelinckx, N. De Kimpe, and A. Šačkus, “Synthesis and reactions of 1-amino-1,5,6,10b-tetrahydroimidazo[2,1-a]isoquinolin-2(3H)-ones,” ARKIVOC, no. 6, pp. 48–62, 2009.
@article{505622, abstract = {{1-Amino-1,5,6,10b-tetrahydroimidazo[2,1-a]isoquinolin-2(3H)-ones, as previously unknown ring-annelated isoquinolines with a 3-aminoimidazolidin-4-one scaffold, were selectively prepared upon reacting 2-carbamoylmethyl- or 2-ethoxycarbonylmethyl-3,4-dihydroisoquinolinium salts with hydrazine hydrate. Acylation of the primary amino group with benzoyl chlorides, followed by reductive ring cleavage of the annelated 4-imidazolidinone ring and final cyclodehydration of the N,N'-diacylhydrazines resulted in the synthesis of 1-methyl-2(5-aryl-[1,3,4]oxadiazol-2-ylmethyl)-1,2,3,4-tetrahydroisoquinolines which are of interest due to their potential use as bioisosteres of biologically active N-aryl-2-(1-methyl-3,4-dihydro-1H-isoquinolin-2-yl) acetamides.}}, author = {{Solovjova, Joana and Martynaitis, Vytas and Holzer, Wolfgang and Mangelinckx, Sven and De Kimpe, Norbert and Šačkus, Algirdas}}, issn = {{1551-7004}}, journal = {{ARKIVOC}}, keywords = {{Ring annelation,isoquinolines,1-amino-1,5,6,10b-tetrahydroimidazo[2,1-a]isoquinolin-2(3H)-ones,hydrazides,1,3,4-oxadiazoles,ISOQUINOLINE ALKALOIDS,ASYMMETRIC-SYNTHESIS,BETA-PHENYLETHYLAMINES,DERIVATIVES,2-AMINO-1,3,4-OXADIAZOLES,REARRANGEMENT,CONDENSATION,ACID}}, language = {{eng}}, number = {{6}}, pages = {{48--62}}, title = {{Synthesis and reactions of 1-amino-1,5,6,10b-tetrahydroimidazo[2,1-a]isoquinolin-2(3H)-ones}}, url = {{http://doi.org/10.3998/ark.5550190.0010.606}}, year = {{2009}}, }
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