Morpholino nitril

The nitrile 153 similarly can be formed below - 105°C by a kinetically controlled deprotonation with LDA, but on warming above -100°C it readily rearranges to the thermodynamically more stable vinyllithium derivative 154 [77AG(E)853]. In contrast the morpholino derivative 155 is... 

Transformation of both the ester and nitrile derivatives 726 or 727 into pyrano[2,3-t7 pyridazines 728 or 729, respectively, by treatment with dilute HCl at room temperature involved nucleophilic displacement of the morpholine group by the hydroxyl group with an acidic hydrolysis followed by intramolecular iminolactonization and then hydrolysis of the formed imino group to a carbonyl group. Compounds 726 and 727 were prepared by Vilsmeier-Haack formylation of 2-methyl-5-morpholino-3(2/7)-pyridazinone 724 followed by condensation of the resulting product 725 with either ethyl a-cyanoacetate or malononitrile in EtOH (Scheme 34) <1994H(37)171>. 

Amino-hydra zino-methylen)- -diester E15/1, 784 (CC13 -+ NH-NH2) [(Amino-morpholino-methylen-amino)-arylamino-methylen]- -ethylesternitril- E15/2, 2140 (SR - N = CR-NH2) (Amino-organooxy-methylen)- -ester-nitril E15/2, 1804 [(NC)2NH - COOR + R - OH] (3-Anilino-2-propinyliden)- -nitril E15/3, 3366... 

Glyoxyisaure (2,4-Dimethyl-phenyl)- -nitril E5, 1446 (ArH + NC-CN/HF) 1,3,5-Hexatriin 1-Morpholino-E19d, 159 (red. Cl2-Eliminie-rung)... 

Isophthaisaure 2,6-Dimethyl-4-dimethylamino- -bis-nitriloxid E5, 1591 (aus Bis-oxim) Malonsaure (Amino-benzylamino-methylen)- -methylester-nitril E15/2, 2156 (CC13 - NH-R) I,3i4-Oxadiazol 5-Morpholino-2-phenyl- E8c, 573 (Ar — CO — NH-NH-CO-NR2/POCl3) Phthalazine l,4-Dihydroxy-6-pyrrolidino- E9a, 752 (subst. Phthalanhydrid + N2H4) lH-Pyrazol 5-Carboxy-l-methyl-4-(4-methyl-anilino)- E8b, 633 (4-Br -> 4-NH-Ar)... 

Aminocarl )onyl-2,2-dimcthyl-l-(2-methyl-l-propenyl)- 1789 1 -Methyl-2-morpholino-l -vinyl- 130 I lexan-6-al-l -nitrile... 

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