[3+2] Cycloaddition reactions of arylallenes with C-(N-arylcarbamoyl)- and C,C-bis(methoxycarbonyl)nitrories and subsequent rearrangements

J. Malinina, T.Q. Tran, A.V. Stepakov, V.V. Gurzhiy, G.L. Starova, R.R. Kostikov, A.P. Molchanov

Research output

14 Citations (Scopus)

Abstract

The first example of 1,3-dipolar cycloaddition reactions of nitrones with arylallenes is described. C-Carbamoylnitrones react with the C1-C2 double bond of arylallenes affording the corresponding 4-methyleneisoxazolidines in good yields. N-Aryl-C,C-bis(methoxycarbonyl)nitrones usually gave rearranged products: mixtures of 4,5-dihydro-4-oxo-1H-benzo[b]azepine-2,2(3H)dicarboxylates and 4-oxo-1, 5-diarylpyrrolidine-2,2-dicarboxylates. (C) 2014 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)3663-3666
Number of pages4
JournalTetrahedron Letters
Volume55
Issue number27
DOIs
Publication statusPublished - 2014

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Cycloaddition
Cycloaddition Reaction
Azepines
nitrones

Cite this

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title = "[3+2] Cycloaddition reactions of arylallenes with C-(N-arylcarbamoyl)- and C,C-bis(methoxycarbonyl)nitrories and subsequent rearrangements",
abstract = "The first example of 1,3-dipolar cycloaddition reactions of nitrones with arylallenes is described. C-Carbamoylnitrones react with the C1-C2 double bond of arylallenes affording the corresponding 4-methyleneisoxazolidines in good yields. N-Aryl-C,C-bis(methoxycarbonyl)nitrones usually gave rearranged products: mixtures of 4,5-dihydro-4-oxo-1H-benzo[b]azepine-2,2(3H)dicarboxylates and 4-oxo-1, 5-diarylpyrrolidine-2,2-dicarboxylates. (C) 2014 Elsevier Ltd. All rights reserved.",
author = "J. Malinina and T.Q. Tran and A.V. Stepakov and V.V. Gurzhiy and G.L. Starova and R.R. Kostikov and A.P. Molchanov",
year = "2014",
doi = "10.1016/j.tetlet.2014.04.107",
language = "English",
volume = "55",
pages = "3663--3666",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier",
number = "27",

}

TY - JOUR

T1 - [3+2] Cycloaddition reactions of arylallenes with C-(N-arylcarbamoyl)- and C,C-bis(methoxycarbonyl)nitrories and subsequent rearrangements

AU - Malinina, J.

AU - Tran, T.Q.

AU - Stepakov, A.V.

AU - Gurzhiy, V.V.

AU - Starova, G.L.

AU - Kostikov, R.R.

AU - Molchanov, A.P.

PY - 2014

Y1 - 2014

N2 - The first example of 1,3-dipolar cycloaddition reactions of nitrones with arylallenes is described. C-Carbamoylnitrones react with the C1-C2 double bond of arylallenes affording the corresponding 4-methyleneisoxazolidines in good yields. N-Aryl-C,C-bis(methoxycarbonyl)nitrones usually gave rearranged products: mixtures of 4,5-dihydro-4-oxo-1H-benzo[b]azepine-2,2(3H)dicarboxylates and 4-oxo-1, 5-diarylpyrrolidine-2,2-dicarboxylates. (C) 2014 Elsevier Ltd. All rights reserved.

AB - The first example of 1,3-dipolar cycloaddition reactions of nitrones with arylallenes is described. C-Carbamoylnitrones react with the C1-C2 double bond of arylallenes affording the corresponding 4-methyleneisoxazolidines in good yields. N-Aryl-C,C-bis(methoxycarbonyl)nitrones usually gave rearranged products: mixtures of 4,5-dihydro-4-oxo-1H-benzo[b]azepine-2,2(3H)dicarboxylates and 4-oxo-1, 5-diarylpyrrolidine-2,2-dicarboxylates. (C) 2014 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetlet.2014.04.107

DO - 10.1016/j.tetlet.2014.04.107

M3 - Article

VL - 55

SP - 3663

EP - 3666

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 27

ER -