3- Amino-9-methoxy-10-phenyl

Pyrazolin-5-one, 3-amino-1 -phenyl- C NMR, 5, 194 (70JCS(C)1842) 2-Pyrazolin-5-one, 4,4-diethyl-3-methoxy- C NMR, 5, 194 (80CB3910)... 

The methoxy group is replaced in the reaction of 3-methoxy-5-phenyl-1,2,4-triazine 1-oxide 46 with ammonia, resulting in 3-amino-5-phenyl-1,2,4-triazine 1-oxide 47. The treatment of 3-methoxy-1,2,4-triazine 1-oxide 20 with hydrazine leads to 3-hydrazino-1,2,4-triazine 1-oxide 48 (71JOC787). 

Isocyanide, benzyl, 55, 98 Isocyanide, butyl-, 55, 98 Isocyanide, cyclohexyl-, 55, 98 ISOCYANIDE, 1,1-dimethylethyl- [Isocy-amde, tert-butyl-], 55,96 Isocyanide, dodecanyl- 55,98 Isocyanide, ethyl- 55,98 Isocyanide, methyl-, 55, 98 Isocyanide, phenyl-, 55, 98 1//Isoindole 1,3(2//) dione, 2 amino [Phthahmidc, N-amino-], 55, 115 1//-ISOINDOLE-1,3(2//)-DIONE, trans-( )-2-(2,3-diphenyl-l-aziridinvl)-[Azindine, frans-2,3-diphenyl-l-phthalimido-], 55, 115 ISOXAZOLE, 3-(4-chlorophenyl)-5-(4-methoxy phenyl)-, 55, 39 Isoxazole 5-(4-chlorophenyl)-3-(4-meth-oxyphenyl)-, 55, 42... 

Schwer reduzierbare kon jugierte Nitro-olefine, z. B. phenolische 2-Nitro-1-phenyl-propen-Derivate, werden zweckmaBig mit Natrium-bis-[2-methoxy-athoxy]-di-hydrido-aluminat zu den 2-Amino-1 -phenyl-propanen umgesetzt12 ... 

Amino-l-(3-chlor-5-hydroxy-4-methoxy-phenyl)-athanol-HydrochIorid 69% d.Th. F 195°... 

Methyl-phenyIthio)-(4-nitro-phenyl)- 700 (2-Nitro-phcnyl)-(2-hydroxy-5-methyl-phenyl)- 693 (2-Nitro-phenyl)-(4-methoxy-phenyl)- 693 (2-Nitro-phenyl)-(4-methyl-phenyl)- 693 Phenyl-(4-amino-phenyl)- 568 Ph en yl-(4-formyl-phenyl) -... 

AthyI-(4-amino-phcnyl)- 684 Athyl-benzyl- 500 Bis-[4-brom-phenyI]- 572 Bis-[4-chlor-phenyl]- 488 Bis-[4-hydroxy-phenyl]- 572 Bis-14-methoxy-phenyl]- 572 Bis-[4-methyl-phenyl]- 572 Bis-[4-nitro-phenyl]- 572 a-Brom- 534f. 

CN [3-[[2-methoxy-4-[[[(2-methylphenyl)sulfonyl]amino]carbonyl]phenyl]methyl]-l-methyl-lH-indol-5-yl]carbamic acid cyclopentyl ester... 

No stereoselectivity was observed in the formation of a 1 1 diastereomeric mixture of 2-hydroxy-2-phenylethyl p-tolyl sulfoxide 145 from treatment of (R)-methyl p-tolyl sulfoxide 144 with lithium diethylamide . However, a considerable stereoselectivity was observed in the reaction of this carbanion with unsymmetrical, especially aromatic, ketones The carbanion derived from (R)-144 was found to add to N-benzylideneaniline stereoselectivity, affording only one diastereomer, i.e. (Rs,SJ-( + )-iV-phenyl-2-amino-2-phenyl p-tolyl sulfoxide, which upon treatment with Raney Ni afforded the corresponding optically pure amine . The reaction of the lithio-derivative of (-t-)-(S)-p-tolyl p-tolylthiomethyl sulfoxide 146 with benzaldehyde gave a mixture of 3 out of 4 possible isomers, i.e. (IS, 2S, 3R)-, (IS, 2R, 3R)- and (IS, 2S, 3S)-147 in a ratio of 55 30 15. Methylation of the diastereomeric mixture, reduction of the sulfinyl group and further hydrolysis gave (—)-(R)-2-methoxy-2-phenylacetaldehyde 148 in 70% e.e. This addition is considered to proceed through a six-membered cyclic transition state, formed by chelation with lithium, as shown below . ... 

The thermal cyclization of [(3-chloro-4-fluorophenyl)amino][4-methoxy-phenyl)methylthio]methylenemalonate (789, R = Cl, R1 = 4-MeOC6H4) in diphenyl ether at 250°C for 3 min gave 2-substituted quinoline-3-carbox-ylate (790, R = Cl, R = 4-MeOC6H4) in 66% yield (82EUP58392). 

Cohare and co-workers reported that aristolactam BU (22) was prepared, following Kupchen s method, by Perkin condensation of 6-bromo-3,4-di-methoxy phenyl acetic acid (119) and o-nitrobenzaldehyde (120) (Scheme 14). The 2-bromo-4,5-dimethoxy-2 -nitro-ds-stilbene-a-carboxylic acid (121) was obtained. The nitro group of 121 was reduced with ferrous sulfate and ammonium hydroxide, and the resulting 2-bromo-4,5-dimethoxy-2 -amino-cw-stilbene-a-carboxylic acid (122) without purification was submitted to the Pschorr phenanthrene synthesis to yield l-bromo-3,4-dimethoxyphen-anthrene-lO-carboxylic acid (123). The phenanthrylamine 124 was prepared from 123 via a Schmidt reaction, and, by treatment with n-butyllithium and CO2, 124, afforded 22 (42). 

In Gegenwart von Zinkchlorid erhalt man aus 4-Amino-3-(4-methoxy-phenyl)-furazan mit Benzaldehyd 4-Benzylidenamino-3-(4-methoxy-phenyl)-furazan (97%)242. 

Benzylidenamino-3-(4-methoxy-phenyl)-furazan242 1,91 g (10 mmol) 4-Amino-3-(4-methoxy-phenyl)-fu-razan werden mit 1 ml Benzaldehyd und einer Spatelspitze wasserfreien Zinkchlorids in 20 ml Benzol 4 h unter Riickfl. gekocht. Nach Abdestillieren des Losungsmittels wird aus Benzol umkristallisiert Ausbeute 2,71 g (97%) Schmp. 95-98° (farblose Prismen). 

HQ OCH3 4- (Dimethylamino-methylen) -amino -3- (4-methoxy-phenyl)-... 88 86-88... 

Weitere Beispiele fur diese Art der Mitsunobu-Reaktion sind die Umwandlung eines 2,2-Diaryl-ethanols in 2-Amino-I-(4-benzyloxy-phenyl)-l-(2-benzyloxy-3-methoxy-phenyl)-ethan2 und die Umwandlung von 5-Hydroxy-2-methyl-l-hexen-3-in in 5-Phthalimido-2-methyl-l-hexen-3-in, das (wie oben formuliert) in 5-Amino-4-ethyl-l-hydroxy-2-methyl-2,3-hexadien ubergefuhrt werden kann3 ... 

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