ν-Triazolines. Part 42. Study on the reactivity of 4,5-dihydro-1-(6-methyl-2-oxo-2H-pyran-4-yl)-5-morpholino-ν-triazoles. Synthetic approach to pyrano[4,3-b]pyrrol-4(1H)-ones

Emanuela Erba; Donato Pocar; Pasqualina Trimarco

doi:10.1039/B008531F

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ν-Triazolines. Part 42.¹ Study on the reactivity of 4,5-dihydro-1-(6-methyl-2-oxo-2H-pyran-4-yl)-5-morpholino-ν-triazoles. Synthetic approach to pyrano[4,3-b]pyrrol-4(1H)-ones

Emanuela Erba,^a Donato Pocar^a and Pasqualina Trimarco*^a

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* Corresponding authors

^a Istituto di Chimica Organica, Facoltà di Farmacia e Centro Interuniversitario di Ricerca sulle Reazioni Pericicliche e Sintesi di Sistemi Etero e Carbociclici, Università di Milano, Via Venezian 21, Italy
E-mail: trimarco@mailserver.unimi.it

Abstract

Pyrolysis of 4-aryl-5-morpholino-4,5-dihydrotriazoles 3 affords two products: pyrano[4,3-b]pyrrol-4(1H)-ones 4 and arylacetamidines 5. The reaction mechanism of this transformation is discussed and reaction conditions optimized to enhance the formation of pyrrole-fused pyran-2-one derivatives 4. 2-Aminoaziridines are considered to be key intermediates in this transformation.

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Article information

DOI: https://doi.org/10.1039/B008531F
Article type: Paper
Submitted: 23 Oct 2000
Accepted: 29 May 2001
First published: 28 Jun 2001

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J. Chem. Soc., Perkin Trans. 1, 2001, 1723-1728

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ν-Triazolines. Part 42. Study on the reactivity of 4,5-dihydro-1-(6-methyl-2-oxo-2H-pyran-4-yl)-5-morpholino-ν-triazoles. Synthetic approach to pyrano[4,3-b]pyrrol-4(1H)-ones

E. Erba, D. Pocar and P. Trimarco, J. Chem. Soc., Perkin Trans. 1, 2001, 1723 DOI: 10.1039/B008531F

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Journal of the Chemical Society, Perkin Transactions 1