STUDIES IN THE ACRIDINE SERIES. VI. THE REACTION OF CERTAIN 9-FORMYLACRIDINES WITH 3-DI-n-BUTYL-AMINOPROPYLMAGNESIUM CHLORIDE

Abstract

1. The synthesis of three new amino earbinols possessing strong plasmodicidal activity, and derived from various 9-formylacridines is described.2. The formation of nitrones through the condensation of aromatic nitroso compounds with reactive methylene groups has been confirmed.

Vinyl azides in heterocyclic synthesis. Part 7. Synthetic studies on the cytotoxic marine alkaloid amphimedine

“…It was intended at the outset that the E-ring of amphimedine would now be added by a Diels-Alder reaction of a suitable azadiene. Specifically, the 2-azadiene (7) introduced recently by…”

“…Condensation of the aldehyde (2) with methyl azidoacetate gives the vinyl azide (3) which on thermolysis in xylene gives the pyridoacridines (4) and (5) in high yield (78% and 19% respectively); this represents the first cyclisation of a vinyl nitrene to a peri-position. Oxidation of the major pyridoacridine (4), or of the mixed pyridoacridines (4) and (5), with manganese dioxide gives the pyridoacridone (6), but neither (6) nor the analogous isopropyl ester (9) undergoes Diels-Alder reaction with the azadiene (7).…”

Intramolecular Coordination in Organometallic Compounds of Groups 2, 12, and 13

“…The [(dimethylamino)methyl]phenyl ligand and the l,3-bis[(dimethylamino)methyl]phenyl ligand have been used extensively during the last decade as intramolecular coordinating ligands for many different (transition) metals. 44 From l-bromo-2-[(dimethylamino)methyl]benzene, the corresponding Grignard reagent 37 (Scheme 25) was formed readily and in Scheme 25 R1 MgBr R2 R1 = CH2NMe2, R2 = H (37) R1 = R2 = CH2NMe2 (38) quantitative yield, while the meta and para derivative did not react under analogous conditions. 45 In our group, the Grignard reagents 37 and 38 (Scheme 25) were prepared to determine the effects of IC upon the position of the Schlenk equilibrium with the corresponding diarylmagnesium compounds (Scheme 26).46 Scheme 26 R'=CH2NMe2,R2 = H (39) R1 = R2 = CH2NMej (40) Both compounds were formed from the reactions of the corresponding bromides with magnesium in THF in quantitative yield.…”

“…With bis[2,6-bis[(dimethylamino)methyl]phenyl]mercury, the corresponding exchange reaction did not Scheme 27 take place (not even at 60 °C), probably because of steric reasons. Therefore, 40 was prepared from the Grignard compound 38 and the corresponding organolithium compound (Scheme 27).…”

CARBINOLAMINES OF THE TYPE R-CHOH-CH2NR2 DERIVED FROM 7- AND 8-ACETYL-1,2,3,4-TETRAHYDROACRIDINES AS PLASMODICIDES1

“…of 3 A aluminum isopropoxide (8)6 during 50-60 mins, (steam-bath). Propanol-2 was distilled (vacuo) and the cooled residue was shaken into ether in the presence of excess 2 A NaOH. The waterwashed and dried ether solution afforded 7.3 g. of a syrup, a cold acetone (20 ml.)…”