A series of α,α ‐dimethoxydihydrofurans have been prepared and subjected to various acidic and neutral hydrolysis conditions in attempts to prepare conjugated enediones in a stereospecific manner. Isomerization of the 3‐hexene‐2,5‐diones and rearrangements of other enediones to β,γ‐unsaturated‐γ‐lactones have been uncovered. Methods of assignment of stereochemical configuration to the enediones are evaluated; reaction with hydrazine hydrate in the absence of acid is proposed as a useful criterion.
once from EtOH, gave 0.90 g (27.5%), the salt mp 210-212°d ec. Anal. (CuH,4C1N04S) C, H, Cl, N, .-To a cold soln (0-5°) of 23.8 g of (0.073 mole) of 2-chloro-5-aminobenzophenone in 73 ml of AcOH and 25 ml of coned HC1 was added slowly 5.58 g (0.685 mole) of NaN02 in 9.5 ml of H20. This mixt was stirred for 0.5 hr at 0-5°. Then was added 17.3 g (0.27 mole) of S02 in 51 ml of AcOH contg 2.9 g (0.017 mole) of CuCU in 5.2 ml of H2O. This mixt was allowed to warm to room temp with stirring during 1 hr and poured into ice water. The solid was collected yielding 21.27 g (92.5%) of pale yellow solid, mp 86.5-89°. A sample was recrystd from methylcyclohexane, mp 90.5-92°. Anal. (Ci,H8C1,08S) C, H, Cl, S. l,3-Dihydro-7-(methanesuIfonamido)-l-methyl-5-phenyl-2Hl,4-benzodiazepin-2-one ( 16).-To a slurry of 2.65 g (0.01 mole) of 7-amino-1,3-dihydro-l-methyl-5-phenyl-2fl-l,4-benzodiazepin-2-one11 in 20 ml of dry pyridine was added portionwise 1.37 g (0.012 mole) of MeS02Cl. The mixt was stirred for 1.0 hr at room temp and then warmed on a steam bath for 0.5 hr. Evapn of the reaction mixt in vacuo gave a syrup which was taken up in CHCh, washed (H20), dried (MgS04), and reevapd to give 4.3 g (11) O.
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