Cycloaddition reaction with methylnitrone

Fornefeld, E. J.; Pike, Andrew

doi:10.1021/jo01319a038

Cited by 28 publications

(2 citation statements)

References 2 publications

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“…The major product was purified by flash chromatography using CHC13 as eluant; yield 0.11 g (61%), m.p. 197-198 "C; 6 (8), 132 (18), 130 (30), 119 (18), 104 (22), 91 (32), and 77 (100); v,,,(Nujol) 1608 (w, E N ) (Found: C, 60.75; H, 3.95; N, 36.1. C14HllN7 requires 60.64; H, 4.00, N, 35.36%; the value for N was consistently found to be high).…”

Section: (19)mentioning

confidence: 99%

N-substituted benzotriazoles as synthons for 1,3-dipoles

Katritzky¹,

Hitchings²,

Zhao³

1990

J. Chem. Soc., Perkin Trans. 1

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N-Bis(benzotriazo1-1 -ylmethyl) hydroxylamine has been shown to be an effective synthon for the nitrone 1,3-dipole. Regio-and stereo-specific cycloaddition with several dipolarophiles to furnish substituted 2-(benrotriazol-I -ylmethyl) isoxazolidines is described. Subsequent replacement of the benzotriazole entity is reported, and reaction of the cycloadducts with perchloric acid is shown to yield isoxarolidines without nitrogen substitution. The synthesis of the novel tricyclic ring system 12-oxa-l,3-diazatricyclo[7.2.1 .O&*]dodec-5-ene is also reported. Benzotriazol-1 -ylmethylene( benzotriazol-I -ylmethyl)amine does not act as a synthon for the azomethine ylide.1,3-Dipolar cycloadditions are of the greatest importance for the synthesis of 5-membered heterocyclic compounds. '-' The reaction is versatile in regard to the range of heterocycles that may be prepared, generally high yielding, and both regio-and stereo-specific in the vast majority of reported cases. In accord with such desirable characteristics, 1,3-dipolar cycloadditions are finding increasing use in synthetic organic chemistry. New methods by which 1,3-dipoles may be generated, and demonstrating the successful cycloaddition of such species, is of great current interest. The present paper reports our preliminary findings in the use of bis(benzotriazo1-1-ylmethy1)amine and bis(benzotriazo1-1 -ylmethyl)hydroxylamine as sources of 1,3dipoles.The use of N-substituted benzotriazoles as synthetic intermediates in the preparation of many classes of organic compounds, such as amines, hydroxylamines,8-'0 and amides,' ' J has been reported previously. Generally such methods have relied on the ease with which benzotriazolate may be displaced by suitable nucleophiles. In particular, when the benzotriazolyl substituent is a to a heteroatom with an available lone pair of electrons (nitrogen or sometimes oxygen), solutions of such adducts frequently exist in equilibrium with their ionised counterparts (Scheme 1).l3*l4 Scheme 1.

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Section: (19)mentioning

confidence: 99%

N-substituted benzotriazoles as synthons for 1,3-dipoles

Katritzky¹,

Hitchings²,

Zhao³

1990

J. Chem. Soc., Perkin Trans. 1

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“…methylenenitrones) with mono-and 1,1disubstituited alkenes has only been investigated to a limited extent. 15,17,[18][19][20][21] The reactions involving methylenenitrones and 1,2-disubstituted alkenes are scarcely even mentioned in the literature. 19 Most recently, we have reported 17 a systematic study detailing the regio-and stereo-chemical features associated with the cycloaddition of the chiral methylenenitrone 2 (R = H) to a series of mono-and 1,1disubstituted alkenes.…”

mentioning

confidence: 99%

The Regio-and Stereo-Chemistry of 1,3-Dipolar Cycloaddition of a Chiral Methylenenitrone to 1,2-Disubstituted Alkenes

Ali

Iman

2008

Journal of Chemical Research

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A study of regio-and stereo-selectivity in the cycloaddition reactions of a series of symmetrical and unsymmetrical 1,2-disubstituted alkenes to the chiral, internally H-bonded N-(2-hydroxy-1-phenyl)methylenenitrone, has been carried out. The regioselectivity observed in the addition reactions is explained in terms of frontier orbital interactions. The alkenes having a hydroxymethyl substituent at the allylic position are found to undergo regio-as well as highly stereo-selective cycloaddition reactions in the presence of anhydrous magnesium bromide.

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N-Methylhydroxylamine

Whitney¹

2001

Encyclopedia of Reagents for Organic Synthesis

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Cycloaddition reaction with methylnitrone

Cited by 28 publications

References 2 publications

N-substituted benzotriazoles as synthons for 1,3-dipoles

N-substituted benzotriazoles as synthons for 1,3-dipoles

The Regio-and Stereo-Chemistry of 1,3-Dipolar Cycloaddition of a Chiral Methylenenitrone to 1,2-Disubstituted Alkenes

N-Methylhydroxylamine

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