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Synlett 2012(6): 885-888  
DOI: 10.1055/s-0031-1290609
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Studies on the Synthesis of 2-Alkyl-5-aryl-1,3,4-oxadiazolines from N-Acylhydrazones

Eugenia Marqués-Lópeza,, Elena Díeza, Eloísa Martín-Zamoraa, Eleuterio Álvarezb, Rosario Fernández*a, José M. Lassaletta*b
a Departamento de Química Orgánica, Universidad de Sevilla, Apdo. de Correos N˚ 1203, 41071 Seville, Spain
e-Mail: ffernan@us.es;
b Instituto de Investigaciones Químicas (CSIC-US), Américo Vespucio 49, 41092 Seville, Spain
Fax: +34(95)4460565; e-Mail: jmlassa@iiq.csic.es;
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Received 24 November 2011
Publikationsdatum:
15. März 2012 (online)

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Abstract

Reaction of N-acylhydrazones with benzyloxyacetyl chloride in the presence of i-Pr2EtN affords new 1,3,4-oxadiazolines in excellent yields (72-95%), under mild reaction conditions and in short reaction times. The structures of the products were confirmed by single-crystal X-ray diffractometry. A plausible reaction mechanism is proposed.

Key words

N-acylhydrazones - oxadiazolines - benzyloxyacetyl chloride - acylation - heterocycles

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1

Present address: Laboratorio de Síntesis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, 50009 Zaragoza, Spain

13

Crystal data for 7e (CCDC 850772): C20H21N3O5; M = 383.40; monoclinic; a = 33.9831 (8) Å, b = 6.14820 (10) Å, c = 20.2932 (5) Å, α = 90.00˚, β = 118.3420 (10)˚, γ = 90.00˚; V = 3731.71 (14) ų; T = 100 (2) K; space group C2/c; Z = 8; µ(MoK α) = 0.100 mm-¹; 34754 reflections measured, 5690 independent reflections (R int  = 0.0436). The final R 1 values were 0.0474 (I > 2σ(I)). The final wR(F ²) values were 0.1106 (I > 2σ(I)). The final R 1 values were 0.0941 (all data). The final wR(F ²) values were 0.1314 (all data); goodness-of-fit: 1.030.