6533b82efe1ef96bd1294565

RESEARCH PRODUCT

Efficient synthesis and structural analysis of new dioxopiperazine isoquinolines

Inmaculada BerenguerFernando D. SuvireDiego CortesNuria CabedoM. Carmen Ramírez De ArellanoDaniel EnrizM.a. ZamoraNoureddine El AouadAlmudena Bermejo

subject

DiffractionChemistryComputational chemistryOrganic ChemistryDrug DiscoverymedicineAb initioMoietyBiochemistryChloridemedicine.drugIon

description

Abstract We report herein the synthesis of new dioxopiperazine isoquinolines using the Pictet–Spengler cyclisation. Our synthetic strategy for the preparation of two new compounds ( 5 , 6 ), with a tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione moiety was developed in only four steps. To understand better the crucial step of the synthesis reported here, theoretical calculations using semiempirical (PM3), ab initio and DFT computations were carried out on a reduced system model. The structure of chlorohydrate water solvate of tetrahydro (2-piperidinylethyl)-6H-pyrazino [1,2-b]isoquinoline-1,4-dione ( 6·HCl·2H2O ) was determined by X-ray diffraction. Theoretical calculations (RHF/3-21G and RB3LYP/6-31G(d)) were also performed for compound 6 neutralised with a chloride ion.

yearjournalcountryeditionlanguage
2006-05-01Tetrahedron
https://doi.org/10.1016/j.tet.2006.02.065