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Synthesis of 2-[(arylmethylene)amino]cyclopropanecarbonitriles via a two-step ring transformation of 2-(cyanomethyl)aziridines

(2009) SYNTHESIS-STUTTGART. p.1105-1112
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Organization
Abstract
Reaction of 2-(cyanomethyl)aziridines with N-bromosuccinimide in dichloromethane results in the formation of 3-[(arylmethylene)amino]-4-bromobutanenitriles in high yield. The latter beta-amino-gamma-bromobutanenitriles were converted into separable trans- and cis-2-[(arylmethylene)amino]cyclopropanecarbonitriles through a 1,3-cyclization by reaction with potassium tert-butoxide, thus culminating in a two-step ring transformation of 2-(cyanomethyl)aziridines into 2-[(arylmethylene)amino]cyclopropanecarbonitriles.
Keywords
cyclizations, ring opening, carbocycles, amino nitriles, 2-(cyanomethyl)aziridines, BETA-AMINO ACIDS, AMINOCYCLOPROPANE CARBOXYLIC-ACIDS, INTERMEDIATE AZIRIDINIUM SALTS, 2-DIALKYLCYCLOPROPANECARBOXYLIC ACIDS, 1-AMINOCYCLOPROPANECARBOXYLIC ACID, N-CYCLOPROPYLIMINE-1-PYRROLINE PHOTOREARRANGEMENT, 1-AMINO-2, ENANTIOSELECTIVE SYNTHESIS, GAMMA-AMINO, VERSATILE SYNTHESIS, STEREOSELECTIVE-SYNTHESIS

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MLA
Mangelinckx, Sven et al. “Synthesis of 2-[(arylmethylene)amino]cyclopropanecarbonitriles via a Two-step Ring Transformation of 2-(cyanomethyl)aziridines.” SYNTHESIS-STUTTGART 7 (2009): 1105–1112. Print.
APA
Mangelinckx, S., D’hooghe, M., Peeters, S., & De Kimpe, N. (2009). Synthesis of 2-[(arylmethylene)amino]cyclopropanecarbonitriles via a two-step ring transformation of 2-(cyanomethyl)aziridines. SYNTHESIS-STUTTGART, (7), 1105–1112.
Chicago author-date
Mangelinckx, Sven, Matthias D’hooghe, Sietske Peeters, and Norbert De Kimpe. 2009. “Synthesis of 2-[(arylmethylene)amino]cyclopropanecarbonitriles via a Two-step Ring Transformation of 2-(cyanomethyl)aziridines.” Synthesis-stuttgart (7): 1105–1112.
Chicago author-date (all authors)
Mangelinckx, Sven, Matthias D’hooghe, Sietske Peeters, and Norbert De Kimpe. 2009. “Synthesis of 2-[(arylmethylene)amino]cyclopropanecarbonitriles via a Two-step Ring Transformation of 2-(cyanomethyl)aziridines.” Synthesis-stuttgart (7): 1105–1112.
Vancouver
1.
Mangelinckx S, D’hooghe M, Peeters S, De Kimpe N. Synthesis of 2-[(arylmethylene)amino]cyclopropanecarbonitriles via a two-step ring transformation of 2-(cyanomethyl)aziridines. SYNTHESIS-STUTTGART. 2009;(7):1105–12.
IEEE
[1]
S. Mangelinckx, M. D’hooghe, S. Peeters, and N. De Kimpe, “Synthesis of 2-[(arylmethylene)amino]cyclopropanecarbonitriles via a two-step ring transformation of 2-(cyanomethyl)aziridines,” SYNTHESIS-STUTTGART, no. 7, pp. 1105–1112, 2009.
@article{628897,
  abstract     = {Reaction of 2-(cyanomethyl)aziridines with N-bromosuccinimide in dichloromethane results in the formation of 3-[(arylmethylene)amino]-4-bromobutanenitriles in high yield. The latter beta-amino-gamma-bromobutanenitriles were converted into separable trans- and cis-2-[(arylmethylene)amino]cyclopropanecarbonitriles through a 1,3-cyclization by reaction with potassium tert-butoxide, thus culminating in a two-step ring transformation of 2-(cyanomethyl)aziridines into 2-[(arylmethylene)amino]cyclopropanecarbonitriles.},
  author       = {Mangelinckx, Sven and D'hooghe, Matthias and Peeters, Sietske and De Kimpe, Norbert},
  issn         = {0039-7881},
  journal      = {SYNTHESIS-STUTTGART},
  keywords     = {cyclizations,ring opening,carbocycles,amino nitriles,2-(cyanomethyl)aziridines,BETA-AMINO ACIDS,AMINOCYCLOPROPANE CARBOXYLIC-ACIDS,INTERMEDIATE AZIRIDINIUM SALTS,2-DIALKYLCYCLOPROPANECARBOXYLIC ACIDS,1-AMINOCYCLOPROPANECARBOXYLIC ACID,N-CYCLOPROPYLIMINE-1-PYRROLINE PHOTOREARRANGEMENT,1-AMINO-2,ENANTIOSELECTIVE SYNTHESIS,GAMMA-AMINO,VERSATILE SYNTHESIS,STEREOSELECTIVE-SYNTHESIS},
  language     = {eng},
  number       = {7},
  pages        = {1105--1112},
  title        = {Synthesis of 2-[(arylmethylene)amino]cyclopropanecarbonitriles via a two-step ring transformation of 2-(cyanomethyl)aziridines},
  url          = {http://dx.doi.org/10.1055/s-0028-1088000},
  year         = {2009},
}

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