An efficient method of synthesis of isoxazolidine-fused β-lactams via base-promoted cyclization–ring opening of carbamoyl-spirocyclopropane isoxazolidines

T.Q. Tran, R.S. Savinkov, V.V. Diev, G.L. Starova, A.P. Molchanov

Research output

13 Citations (Scopus)

Abstract

1,3-Dipolar cycloadditions of dialkyl-substituted 2-benzylidenecyclopropane-1,1-dicarboxylates and a number of C-carbamoyl nitrones proceed with high efficiency and selectivity with the formation of single isomeric spiro[cyclopropane-1,4-isoxazolidine] cycloadduct. Obtained cycloadducts easily undergo cyclopropyl ring opening-cyclization to form new beta-lactams fused with isoxazolidine ring in high yields. (C) 2013 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)5173-5177
Number of pages5
JournalTetrahedron
Volume69
Issue number25
DOIs
Publication statusPublished - 2013

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Lactams
Cycloaddition
Cyclization
Cycloaddition Reaction
beta-Lactams
nitrones
cyclopropane

Cite this

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title = "An efficient method of synthesis of isoxazolidine-fused β-lactams via base-promoted cyclization–ring opening of carbamoyl-spirocyclopropane isoxazolidines",
abstract = "1,3-Dipolar cycloadditions of dialkyl-substituted 2-benzylidenecyclopropane-1,1-dicarboxylates and a number of C-carbamoyl nitrones proceed with high efficiency and selectivity with the formation of single isomeric spiro[cyclopropane-1,4-isoxazolidine] cycloadduct. Obtained cycloadducts easily undergo cyclopropyl ring opening-cyclization to form new beta-lactams fused with isoxazolidine ring in high yields. (C) 2013 Elsevier Ltd. All rights reserved.",
author = "T.Q. Tran and R.S. Savinkov and V.V. Diev and G.L. Starova and A.P. Molchanov",
year = "2013",
doi = "10.1016/j.tet.2013.04.054",
language = "English",
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pages = "5173--5177",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",
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TY - JOUR

T1 - An efficient method of synthesis of isoxazolidine-fused β-lactams via base-promoted cyclization–ring opening of carbamoyl-spirocyclopropane isoxazolidines

AU - Tran, T.Q.

AU - Savinkov, R.S.

AU - Diev, V.V.

AU - Starova, G.L.

AU - Molchanov, A.P.

PY - 2013

Y1 - 2013

N2 - 1,3-Dipolar cycloadditions of dialkyl-substituted 2-benzylidenecyclopropane-1,1-dicarboxylates and a number of C-carbamoyl nitrones proceed with high efficiency and selectivity with the formation of single isomeric spiro[cyclopropane-1,4-isoxazolidine] cycloadduct. Obtained cycloadducts easily undergo cyclopropyl ring opening-cyclization to form new beta-lactams fused with isoxazolidine ring in high yields. (C) 2013 Elsevier Ltd. All rights reserved.

AB - 1,3-Dipolar cycloadditions of dialkyl-substituted 2-benzylidenecyclopropane-1,1-dicarboxylates and a number of C-carbamoyl nitrones proceed with high efficiency and selectivity with the formation of single isomeric spiro[cyclopropane-1,4-isoxazolidine] cycloadduct. Obtained cycloadducts easily undergo cyclopropyl ring opening-cyclization to form new beta-lactams fused with isoxazolidine ring in high yields. (C) 2013 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tet.2013.04.054

DO - 10.1016/j.tet.2013.04.054

M3 - Article

VL - 69

SP - 5173

EP - 5177

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 25

ER -