Synlett
DOI: 10.1055/a-1308-3773
letter

Synthesis of Spiro Oxazolidinedione Analogues Based on Tandem Multicyclizations of 1,3-Dimethylalloxan and Enaminones in Water

Tina Abbasi
a  Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran
,
b  Department of Chemistry, Kharazmi University, Tehran, Iran
,
c  Department of Chemistry, Tarbiat Modares University, Tehran, Iran
,
Rahman Bikas
d  Department of Chemistry, Imam Khomeini International University, Qazvin, Iran
› Author Affiliations
The financial support of Kharazmi University (grant number D/2047) is gratefully acknowledged.


Abstract

A tandem double-annulation reaction of 1,3-dimethylalloxan with enaminones, generated in situ from alkyl amines and alkyl but-2-ynoates or pent-3-yn-2-ones to give functionalized oxazolidinedione spiro analogues is described. Three of the four carbonyl groups of alloxan have been engaged through a tandem Michael addition, aldol-type condensation, and double intramolecular annulation sequence.

Supporting Information



Publication History

Received: 27 September 2020

Accepted after revision: 11 November 2020

Publication Date:
11 November 2020 (online)

© 2020. Thieme. All rights reserved

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  • 11 Spiro Compounds 4 and 5: General ProcedureA mixture of the appropriate amine 1 (1 mmol) and alkyne 2 (1 mmol) in H2O (5 mL) was stirred at r.t. for 3 h. 1,3-Dimethylalloxan (3; 1 mmol) was then added, and the mixture was stirred for 24 h at r.t. until the reaction was complete (TLC). The H2O was removed by using a rotary evaporator, and the residue was purified by column chromatography [silica gel, hexane–EtOAc (5:1)].Methyl (2E)-(3,7-Dimethyl-2,4,6-trioxo-1-oxa-3,7-diazaspiro[4.4]non-8-ylidene)acetate (4a)Colorless amorphous powder; yield: 0.196 g (73%); mp 200–202 °C (dec.); Rf = 0.55 (25% EtOAc–hexane). IR (KBr): 3090 (=C–H), 1836, 1745, 1743 and 1699 (C=O), 1638 (C=C) cm–1. 1H NMR (300.1 MHz, CDCl3): δ = 3.13 (s, 3 H, NCH3), 3.16 (s, 3 H, NCH3), 3.73 (OCH3, 3 H), 3.55 and 3.90 (d of AB-system, 2 J HH = 19.3, 4 J HH = 1.8 Hz, 2 H, CH2), 5.43 (t, 4 J HH = 1.8 Hz, 1 H, =CH). 13C NMR (75.5 MHz, CDCl3): δ = 169.5, 166.8, 166.5, 153.9, 152.4, 95.4, 82.4, 51.5, 33.5, 28.3, 26.8. Anal. Calcd for C11H12N2O6 (268.23): C, 49.26; H, 4.51; N 10.44. Found: C, 49.47; H, 4.57; N, 10.37.Methyl 3-Methyl-2,4,6-trioxo-8-piperidin-1-yl-1-oxa-3-azaspiro[4.4]non-7-ene-7-carboxylate (5a)Colorless powder; yield: 0.200 g (62%); mp 193–195 °C (dec.); Rf = 0.50 (25% EtOAc–hexane). IR (KBr): 1816, 1727, 1701 and 1667 (C=O), 1592 (C=C) cm–1. 1H NMR (300.1 MHz, CDCl3): δ = 1.79 (m, 6 H, CH2CH2CH2), 3.01 and 3.24 (AB-system, 2 J HH = 16.6 Hz, 2 H, CH2), 3.12 (s, 3 H, NMe), 3.54 (m, 4 H, CH2NCH2), 3.82 (s, 3 H, OMe). 13C NMR (75.5 MHz, CDCl3): δ = 185.7, 170.9, 170.3, 164.3, 154.4, 103.7, 85.4, 53.2, 51.5, 50.7, 35.7, 26.0, 25.9, 25.2, 23.0. Anal. Calcd for C15H18N2O6 (322.32): C, 55.90; H, 5.63; N, 8.69; Found: C, 56.17; H, 5.60; N, 8.76.
  • 12 CCDC 2034055 contains the supplementary crystallographic data for 4a. These data can be obtained free of charge from the joint CCDC/FIZ Karlsruhe deposition service via www.ccdc.cam.ac.uk/getstructures
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