3-Amino-3-aminomethyl

Fig. 14.6 3 -Amino-, 3-aminomethyl-, 3-hydroxy- and 3-hydroxymethylpyrrolidine basic structures for novel bicyclic amines.

Amino-3-aminomethyl- 131 erythro-5-CYi or-4-brom- 12-acetoxy- 564 1,2-Dideutero- 104... 

Tables Densities and thermal characteristics of substituted amino, aminomethyl, and polymethyl tetrazolium salts...

The A/-carboxyl group is lost duting the reaction, and no additional deprotection step is requited (104). Benzene reacts with A/-carboxyglyciae anhydride to give aminomethyl phenyl ketone however, it does not react with other A/-carboxy-a-amino acid anhydrides (105). 

Table 3 gives the corresponding physical properties of some commercially important substituted pyridines having halogen, carboxyHc acid, ester, carboxamide, nitrile, carbiaol, aminomethyl, amino, thiol, and hydroxyl substituents. 

Pyrimido[4,5- f]pyrimidines may be used as pyrimidine precursors. Thus, the dihydro derivative (736) undergoes alkaline hydrolysis to the amide (737 R = PrCO) which may be deacylated in ethanolic hydrogen chloride to give 5-aminomethyl-2-propylpyrimidin-4-amine (737 R = H) (64CPB393) rather similarly, the pyrimidopyrimidinedione (738) reacts with amines to give, for example, 6-amino-5-benzyliminomethyl-l,3-dimethylpyrimidine-2,4(lFf,3Ff)-dione (739 R = CH2Ph) or the hydrazone (739 R = NH2) (74JCS(Pl)1812). 

In many cases, substituents linked to a pyrrole, furan or thiophene ring show similar reactivity to those linked to a benzenoid nucleus. This generalization is not true for amino or hydroxyl groups. Hydroxy compounds exist largely, or entirely, in an alternative nonaromatic tautomeric form. Derivatives of this type show little resemblance in their reactions to anilines or phenols. Thienyl- and especially pyrryl- and furyl-methyl halides show enhanced reactivity compared with benzyl halides because the halogen is made more labile by electron release of the type shown below. Hydroxymethyl and aminomethyl groups on heteroaromatic nuclei are activated to nucleophilic attack by a similar effect. 

Jap-KIingermarm reactions, 4, 301 oxidation, 4, 299 reactions, 4, 299 synthesis, 4, 362 tautomerism, 4, 38, 200 Indole, 5-amino-synthesis, 4, 341 Indole, C-amino-oxidation, 4, 299 tautomerism, 4, 298 Indole, 3-(2-aminobutyl)-as antidepressant, 4, 371 Indole, (2-aminoethyl)-synthesis, 4, 278 Indole, 3-(2-aminoethyl)-synthesis, 4, 337 Indole, aminomethyl-reactions, 4, 71 Indole, 4-aminomethyl-synthesis, 4, 150 Indole, (aminovinyl)-synthesis, 4, 286 Indole, 1-aroyl-oxidation, 4, 57 oxidative dimerization catalysis by Pd(II) salts, 4, 252 Indole, 1-aroyloxy-rearrangement, 4, 244 Indole, 2-aryl-nitration, 4, 211 nitrosation, 4, 210 synthesis, 4, 324 Indole, 3-(arylazo)-rearrangement, 4, 301 Indole, 3-(arylthio)-synthesis, 4, 368 Indole, 3-azophenyl-nitration, 4, 49 Indole, 1-benzenesulfonyl-by lithiation, 4, 238 Indole, 1-benzoyl photosensitized reactions with methyl acrylate, 4, 268 Indole, 3-benzoyl-l,2-dimethyl-reactions... 

Attempts were made to perform heterocyclization with 4-phenylethynyl- and 4-ethynyl-5-aminomethyl-l,3-dimethylpyrazole where, on the one side, a strained six-membered ring can be formed, and, on the other side, the aliphatic amino group is more nucleophilic than the aromatic (Scheme 112). However, all attempts to cyclize the ethynylpyrazole and its phenyl analog failed (86TH1). 

Reaction of 2-amino-4/f-pyrido[l,2-n]pyrimidin-4-ones 143 with HNMei -HCl and paraformaldehyde in Dowtherm A afforded a mixture of 3-(A,A-dimethylamino)methyl derivatives 144 and bis-compounds 145 (93FES1225). Mannich reaction of 9-hydroxy-2-methyl-4//-pyri-dor],2-nlpyrimidin-4-one (146) yielded 8-aminomethyl derivatives 147 (94KFZ(10)23). 

Amino group of 7-aminomethyl-2-substituted perhydropyrido[l,2-u]pyr-azines were reacted with 2-bromopyridine and 2-chloropyrimidines to give 7-(hetarylamino)methyl derivatives in the presence of Na2C03 in DMF at 100-120°C for 18h in 13-51% yields (00MIP15). An aminomethyl group of... 

The reaction of nitrous acid with the amino group of the /3-amino alcohol—e.g. 1-aminomethyl-cyclopentanol 1—leads to formation of the nitrosamine 4, from which, through protonation and subsequent loss of water, a diazonium ion species 5 is formed " —similar to a diazotization reaction ... 

Thus, an aminium radical from primary or secondary amine will at last form an amino radical instead of an aminomethyl radical. This amino radical will then serve as the only active radical species to initiate the vinyl polymerization. 

Novel isosteres 545 of the antiviral agent acyclovir were synthesized in three stages (84JHC697) by dehydrative coupling of 3-amino-6-aminomethyl[ 1,2,4]triazin-5-(4//)-one with 2-(benzoyloxy)ethoxyacetic acid to give the respective amide that cyclized and deprotected to give 545. It showed no activity against herpes simplex virus types I and II in cell culture (Scheme 112). 

Diamines. Pentaerythrityltriamine [3-Amino-2,2-bis(aminomethyl) propanol (name preferred by CA)], CsHi5N3 0,mw 133.19 prepd in... 

Diboran kann besonders dann zur Reduktion von Nitrilen mit Erfolg eingesetzt werden, wenn Lithiumalanat und auch Lithiumalanat/Aluminiumchlorid nicht die gewunschten Resultate zeigen. Aus tert.-Butyl-malonsaure-dinitril erhalt man z.B. nur durch Reduktion mit Diboran l-Amino-3,3-dimethyl-2-aminomethyl-butan (36—48% d. Th.)2. 

Der. 142 Acyl- 142, 258 Alkyl- 142, 258 Amino- 686 Aminomethyl- 579 Cyan- 579 Dodecanoyl- 258 Dodecyl- 258 Iminomethyl- 579 Nitro- 686... 

RN 1161-88-2 MF C7H,oN20jS C7Hi,N,02S2 MW 417.54 EINECS 214-600-7 CN 4-amino-/7-(aminothioxomethyl)benzenesulfonamide compd. with 4-(aminomethyl)benzenesulfonamide (1 1)... 

Simple 1,2,4-triazole derivatives played a key role in both the synthesis of functionalized triazoles and in asymmetric synthesis. l-(a-Aminomethyl)-1,2,4-triazoles 4 could be converted into 5 by treatment with enol ethers <96SC357>. The novel C2-symmetric triazole-containing chiral auxiliary (S,S)-4-amino-3,5-bis(l-hydroxyethyl)-l,2,4-triazole, SAT, (6) was prepared firmn (S)-lactic acid and hydrazine hydrate <96TA1621>. This chiral auxiliary was employed to mediate the diastereoselective 1,2-addition of Grignard reagents to the C=N bond of hydrazones. The diastereoselective-alkylation of enolates derived from ethyl ester 7 was mediated by a related auxiliary <96TA1631>. 

The Mannich condensation has traditionally been carried out in the presence of water as a three-component condensation involving a carbonyl compound (or related carbon nucleophile), formaldehyde, and a primary or secondary amine. The initial step is a condensation between the latter two reactants to form a mono- or dialkyl(methylene)ammonium ion which subsequently serves as the electrophilic partner in the reaction. With unsymmetrical ketones aminomethylation generally occurs at both positions to give mixtures of isomeric 3-amino ketones. The ratio of the isomers depends strongly on the structure of the ketone, and the more highly branched (3-amino ketone usually predominates. 

These amino acids were initially synthesized by asymmetric aminomethylation of optically pure (R)- and (S)-N-Acyl-4-phenyhnethyl)oxazolidin-2-ones 52 through TiCVenolates (Evans methodology [135]) with (benzoylamino)methylchloride or benzyl N-(methoxymethyl)carbamate [66, 97-99, 104]. Hydrolytic removal of the auxiliary yielded the N-protected (benzoyl or Z) amino acid 54. Deprotection afforded the free amino acid which was converted to the required Boc- or Fmoc-pro-tected derivatives (Scheme 2.7). 

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