Preparation of a range of NNN′N′-tetrasubstituted 1,8-diaminonaphthalenes

Abstract

MeNNMe MeN NMe MeN NMe t 1,8-Bis(dimethylamino)naphthalene has achieved some SCHEME 1 Reagents and yields: (2) H,CO-EtOH-H,O (80%) ; popularity as a non-nucleophilic base, sold by the Aldrich Chem. (ii) Br[CH,],Br-NaHC0,-DMF (250/,), or Br[CH,],Br-NaH-Co. as ' Proton Sponge,' although its usefulness is limited by the T H F (80%) ; (iii) Br[CH,],Br-NaHC0,-diglyme (43%), or Brvery slow rates of proton transfer to it (see references 6 and 13) [CH,],Br-NaH-THF (1%); (iv) Br[CH,],Br-NaHC0,and possibly by its relatively easy oxidation. The name ' Proton diglyme (58%) ; (v) Br[CH,],Br-Na,C03-diglyme (25%) ; (vi) Sponge ' is indeed apt; sponges are not kinetically active in seekaa'-dibromo-o-xylene-Na,CO,-DMF (13%) ; (vii) ClCH,CH,ing water, they merely mop it up when it is presented to them.OCH,CH,Cl-Na,CO,-diglyme (77%)

First structural characterization of guanidine, HNC(NH2)2

“…3 and 4). The N-H … N distance reported for the pure substance (3.070(4) Å ) is in good agreement with our findings (2.978 Å (1) and 3.006 Å (2)). The C-NH 2 and C-NH hydrogen atoms of the guanidine molecules in 1 and 2 were directly located in the crystallographic study using difference Fourier maps.…”

“…{ Preparation of guanidine: guanidine was prepared by adding a THF solution of guanidinium chloride (16.7 mmol, 24 ml) to a THF solution of sodium methanolate (16.8 mmol, 24 ml) using standard Schlenk techniques. Acetonitrile was allowed to slowly diffuse into the solution until crystals suitable for X-ray diffraction formed at 4 uC (1) or 25 uC (2).…”

Two new fluorescent heterocyclic perimidines: first syntheses, crystal structure, and spectral characterization

“…15 It has previously been shown 16 17,18 and 0.15 g (1 mmol) of 4-hydroxy-3-methoxy benzaldehyde in methanol. It was refluxed for 3 hours under nitrogen atmosphere.…”

1,8-Bis(bromomethyl)naphthalene in the synthesis of 1,5-diazacyclodecane and benz[de]isoquinoline proton sponges

“…The key steps leading to these rather unusual products are shown in Scheme 4 and were previously observed at interaction of 23 with 1,2-bis(bromomethyl)benzene providing shorter alkylidene bridge. 12 As seen, all products obtained are originated from spirocyclic intermediate Finally, it is noteworthy, that compounds 9, 15 and 18 represent rather stable analogues of the N-benzylated proton sponges and we did not notice any signs of their decomposition in acidic media. Previously, English investigators failed to measure the basicity of simple representatives of such compounds due to their easy debenzylation on treatment with acids.…”