O-toluamides

Additions of stabilized carbanions to imines and hydrazones, respectively, have been used to initiate domino 1,2-addition/cyclization reactions. Thus, as described by Benetti and coworkers, 2-subshtuted 3-nitropyrrolidines are accessible via a nitro-Mannich (aza-Henry)/SN-type process [165]. Enders research group established a 1,2-addition/lactamization sequence using their well-known SAMP/ RAMP-hydrazones 2-308 and lithiated o-toluamides 2-307 as substrates to afford the lactams 2-309 in excellent diastereoselectivity (Scheme 2.72) [166]. These compounds can be further transformed into valuable, almost enantiopure, dihydro-2H-isoquinolin-l-ones, as well as dihydro- and tetrahydroisoquinolines. 

Amino-5-nitro-o-toluamide (245) and 5-amino-3-nitro-o-toluamide (246), the principal metabolites in the tissues of chickens fed a diet containing the anticoccidic agent Zoalene (247), were shown to deplete in frozen liver tissues stored up to 1 year at —20 °C. Both a- and /i-anorncrs of the conjugate were observed by LC of tissue extracts520. 

Figure 6. Photographs of crystals of benzamide (a) pure (b)-(d) grown in the presence of increasing amounts (from bottorrf to top) of (b) benzoic acid (c) o-toluamid, (d) p-toluamid. The crystals shown in this photograph (and all those following) varied in size from about 0.1 to 5 mm.

Dinitolmide, including the metabolite 3-amino-5-nitro-o-toluamide... 

Thoria catalyst, 735 Tischenko reactions, 318 Tollen s ammoniacal silver nitrate reagent, 330, 1061, 1074 p-Tolualdehyde, 689, 697 o-Toluamide, 798 Toluene, 510, 516, 615 purification of, 173, 174 separation from benzene, 231 p-Toluenesulphinic acid, 821, 826 o-Toluenesulphonamide, 821, 824 p-Toluenesulphonamide, 820, 823 p-Toluenesulphonates, 422, 437, 650, 684 ... 

The dilithio derivative of N-methyl-o-toluamide reacts with aromatic aldehydes and ketones to give hydroxyamides. Thermal cyclization affords 3-phenylisochroman-l-ones (64JOC3514). Spiroannelated isochromanones result when the organolithium compound reacts with fluorenone or alicyclic ketones. 

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