t-Carbinamines, RR'R”CNH<sub>2</sub>. II. Cyanoalkylations and Related Reactions<sup>1</sup>

Luskin, Leo S.; Culver, M. J.; Gantert, G. E.; Craig, Wayne; Cook, R. S.

doi:10.1021/ja01597a049

Cited by 9 publications

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“…The amine (1) was transformed into N-chloro-N-t-butylaminoacetonitrile, n.m.r. (CCI,) 6 [s, 9H, C(CH3),]; U.V. (heptane): 213 ( E 1600), 285 nm (90); satisfactory elemental analysis for C , H, and X.…”

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confidence: 99%

Iminoacetonitriles, a new family of compounds. N-t-butyliminoacetonitrile

Boyer¹,

Dabek²

1970

J. Chem. Soc. D

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N-t-Butyliminoacetonitrile (2) constitutes the first known member of a new family of compounds, the iminoacetonitriles RN =CHCN.IN the probable prebiotic chemical evolution of adenine by pentamerization of hydrogen cyanide, it is assumed that a dimer of the latter is a critical intermediate.l Although it remains undetected, iminoacetonitrile has been a suggested2 dimer of hydrogen ~y a n i d e . ~. ~We describe N-t-butyliminoacetonitrile ( 2 ) , the first known member of the family of N-substituted iminoacetonitriles.Following a general procedure,5 N-t-butylaminoacetonitrile ( l ) , b.p. 60.5-61.5"/7 mm,6 n% 1.4307,6 n.m.r. (CCI,) 8 3.49 p.p.ni.

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confidence: 99%

Iminoacetonitriles, a new family of compounds. N-t-butyliminoacetonitrile

Boyer¹,

Dabek²

1970

J. Chem. Soc. D

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“…4-(Benzyloxy)-a-[jV-benzyl-jV-(4-methoxy-«-methylphenethyl)aminomethyl]-3-(methoxymethyl)benzyl Alcohol Hydrochloride (19). To a cold solution of 10.5 g of 18 in 100 mL of EtOH, 0.5 g of NaBH4 was added with stirring and the mixture was refluxed for 1 h. After decomposition of the excess NaBH4 by adding Me2CO, the reaction mixture was evaporated under reduced pressure.…”

Section: -(Benzyloxy)-a-(tert-butylaminomethyl)-3-(methoxymethyl)benz...mentioning

confidence: 99%

New bronchodilators. Synthesis and bronchodilating activity of some 3-(alkoxymethyl)-.alpha.-(N-substituted aminomethyl)-4-hydroxybenzyl alcohols

Sohda¹,

Fujimoto²,

Tamegai³

et al. 1979

J. Med. Chem.

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A series of 3-(alkoxymethyl)-alpha-(N-substituted aminomethyl)-4-hydroxybenzyl alcohols was synthesized as potential bronchodilators. The ability to prevent effects against histamine-induced bronchoconstriction in guinea pigs was studied to determine their bronchodilating activity. Introduction of a methoxymethyl group in place of the m-hydroxyl group of beta-adrenergic catecholamines afforded compounds especially effective in delaying histamine-induced bronchoconstriction in guinea pigs. Appropriate N-substitution also enhanced the potency of these catecholamine analogues. 4-Hydroxy-3-(methoxymethyl)-alpha-[N-[4-(methoxymethyl)-alpha-methylphenyl]aminoethyl]benzyl alcohol hemifumarate (3r) was the most potent compound in this series.

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