Three-Component One-Pot Synthesis of Functionalized 1,2,3,6-Tetrahydropyrano[4,3-b]pyrroles

Issa Yavari; Manzarbanoo Esnaashari

doi:10.1055/s-2005-861839

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Synthesis 2005(7): 1049-1051
DOI: 10.1055/s-2005-861839

SHORTPAPER

Three-Component One-Pot Synthesis of Functionalized 1,2,3,6-Tetrahydropyrano[4,3-b]pyrroles

Issa Yavari*^a,b, Manzarbanoo Esnaashari^a
^a Department of Chemistry, Science & Research Campus, Islamic Azad University, Ponak, Tehran, Iran
^b Department of Chemistry, Tarbiat Modarres University, PO Box 14115-175, Tehran, Iran
Fax: +98(21)8006544; e-Mail: yavarisa@modares.ac.ir;

Further Information

Publication History

Received 6 December 2004
Publication Date:
09 March 2005 (online)

Abstract
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Abstract

The reactive 1:1 adduct, produced from the reaction between dialkyl acetylenedicarboxylates and 2,6-dimethylphenyl isocyanide, was trapped by methyl 2,4-dioxopentanoate to yield dialkyl 1-(2,6-dimethylphenyl)-4-methyl-2,3-dioxo-1,2,3,6-tetrahydropyrano[4,3-b]pyrrole-6,7-dicarboxylates in moderate yields.

Key words

three component reaction - Ugi reaction - methyl 2,4-dioxopentanoate - 2,6-dimethylphenyl isocyanide - acetylenic esters

References

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Crystallographic data for 2c: C₂₆H₃₁NO₇, F _w = 469.52, monoclinic, space group P2₁/c, Z = 8, a = 9.6209 (10) Å, b = 25.076 (2) Å, c = 20.546 (2) Å, α = 90°, β = 93.822 (3)°, γ = 90°, V = 4945.7 (8) Å³, ρ_calcd = 1.261 g cm^-3, R1 = 0.060, wR2 = 0.1240, -6 ≤ h ≤ 12; -16 ≤ k ≤ 32; -26 ≤ l ≤ 24°; Mo-k_a (l = 0.7107 Å), T = 110 (2) K. The structure factors are available from the author upon request.