| Title |
Synthesis and reactions of 1-amino-1,5,6,10b-tetrahydroimidazo- [2,1-a]isoquinolin-2(3H)-ones / |
| Authors |
Solovjova, Joana ; Martynaitis, Vytas ; Holzer, Wolfgang ; Mangelinckx, Sven ; De Kimpe, Norbert ; Šačkus, Algirdas |
| DOI |
10.3998/ark.5550190.0010.606 |
| Full Text |
|
| Is Part of |
Arkivoc.. Gainesville : ARKAT USA. 2009, vol. 2009, iss. 6, p. 48-62.. ISSN 1551-7004. eISSN 1551-7012 |
| Keywords [eng] |
ring annelation ; isoquinolines ; 1-amino-1,5,6,10b-tetrahydroimidazo[2,1-a]isoquinolin- 2(3H)-ones, hydrazides ; 1,3,4-oxadiazoles |
| Abstract [eng] |
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-1Hisoquinolin- 2-yl)acetamides. |
| Published |
Gainesville : ARKAT USA |
| Type |
Journal article |
| Language |
English |
| Publication date |
2009 |
| CC license |
|
