Primary cycloadducts of 1,10-phenanthrolinium and phthalazinium phenacylides with DMAD

✍ Scribed by Florea Dumitraşcu; Carmen Irena Mitan; Constantin Drăghici; Miron Teodor Căproiu; Dan Răileanu

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 155 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01803-2

✦ Synopsis

Primary cycloadducts cis-2 and trans-6 of monosubstituted cycloimmonium phenacylides 1 and 5 with DMAD have been obtained for the first time. They isomerise stereospecifically and regiospecifically by prototropic rearrangement to dihydro derivatives cis-3 and trans-7, respectively. The new heterocyclic system of pyrrolo[1,2-a][1,10]phenanthroline was illustrated by a series of derivatives (8a-f). The ethyl (8b) and isopropyl (8c) esters exhibit helical chirality by 1 H NMR.