Amines 2-aminobenzaldehyde

Amines, preparation from isothiocyanates, 18, 5 from ketones, 17, 76 m-Aminobenzaldehyde, 13, 28... 

Bismuth(lll) chloride catalyzes the intramolecular hetero-Diels-Alder reaction of aldimines, generated in situ from aromatic amines and the A -allyl derivative of o-aminobenzaldehyde, in acetonitrile at reflux to generate [l,6]naphthyridine derivatives <2002TL1573>. The hetero-Diels-Alder reaction of 3-aryl-2-benzoyl-2-propeneni-triles and enol ethers yields 2-alkoxy, 6-diaryl-3,4-dihydro-2//-pyran-5-carbonitriles (Scheme 29) <1997M1157>. 

Amide reduction with lithium aluminum hydride, 39, 19 Amine oxide formation, 39, 40 Amine oxide pyrolysis, 39, 41, 42 -Aminoacetanilide, 39, 1 Amino adds, synthesis of, 30, 7 2-Amino-4-anilino-6-(chloro-METHYl) -S-TRIAZINE, 38, 1 -Aminobenzaldehyde, 31, 6 hydrazone, 31, 7 oxime, 31, 7 phenylhydrazone, 31, 7 > -Aminobenzoic add, 36, 95 2-Aminobenzophenone, 32, 8 c-Aminocaproic acid, 32, 13 6-Aminocaproic acid hydrochloride,... 

The fusion of 2-aminophenyl ketones or 2-aminobenzaldehydes 39 with urea, guanidine, or carbamates is a useful synthetic method for the preparation of 4-substituted quinazolin-2(l//)-ones 40 and quinazolin-2-amines 46. The cyclization is usually carried out by fusing the reagents without solvent at temperatures above 150"C or in a high-boiling solvent (e.g., Decalin). The yields are generally high. 

Quadridentate ligands can be obtained by condensing suitably substituted aldehydes and ketones with bidentate primary amines, and the resulting Schiff bases closely resemble the porphin ring system. Generally, one of the structural units—N=C—C=N—,—N=C—NHC=N—, N=C—NH—N=C—, —C=N—CH=CH—N=C—, or —C=N— CH2—CH2—N=C—is incorporated into the structure for maximum stability. For example, if or /io-aminobenzaldehyde is condensed with ortho-... 

Acrylonitriles 242 were cyclized to isoquinoline derivatives with amines like aniline in acetic acid to yield isoquinolines 243. The dicyanoethenyl derivative 245 was obtained from 147 and o-aminobenzaldehyde 244. ... 

Amines, preparation fromketones,17,76 m-Aminobenzaldehyde, 13, 28 o-Aminobenzenesoleonic acid, 15, 55 -Aminobenzoic acid, 13, 54 Y-Aminobutymc acid, 17, 4 ot-AltlNO-tSO-BUTYRIC ACID, 11, 4 e-AuiNOCAPROIC ACID, 17, 7 2-AlHNOETHANESULFONIC ACID, 10, 98 2-Aminofluorene, 13, 74 I-AMINO-2-NAPHTHOL HYDROCHLORIDE,... 

Scheme 19.61 Primaiy amine-thiourea catalysed domino Michael-Heniy reaction of 2-aminobenzaldehydes and nitroalkenes.

Chloro-2-aminobenzaldehyde does not self-condense in the presence of nicked II) to form macrocyclic products. This may be connected with the decreasing reactivity of the carbonyl and amine groups under the influence of the chlorine atom [362], In the absence of nickel ions, the corresponding bis-anhydrotrimer was isolated, which is converted into Ni(Cl3TRI)(N03)2-C2H50H on interaction with a nickel(II) salt in ethanol. 

The same group also described a TfOH-catalyzed one-pot synthesis of aminals 81 from o-aminobenzaldehydes 79 and primary aromatic or aliphatic amines 80 (Scheme 28) [111]. Theprotonated imine I worked as hydride acceptor. Almost at... 

Seidel et al. also reported a metal-free one-pot a-amination of cyclic secondary amines 78 with 2-aminobenzaldehyde 77, which efficiently furnished ring-fused... 

More recently, Patil et al. reported a cascade reaction of 2-aminobenzaldehydes and 2-amino benzamides by combining chiral Brpnsted acid and achiral gold catalysis [76]. The attractive optically pure 1,2-dihydroisoquinolines were prepared by chiral phosphoric acid-catalyzed asymmetric condensation of alkyne-tethered aldehydes with 2-aminobenzamides to give rise to the chiral aminal 136, which was followed... 

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