Synlett
DOI: 10.1055/s-0036-1588469
cluster
© Georg Thieme Verlag Stuttgart · New York

Reactions of Nitrosobenzenes with Cyclobutanones by Activation with a Lewis Acid

Yusuke Shima, Emiko Igarashi, Tomoyuki Yoshimura, Jun-ichi Matsuo*
  • Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan   Email: jimatsuo@p.kanazawa-u.ac.jp
This work was supported by JSPS KAKENHI Grant Number 15K07855.
Further Information

Publication History

Received: 26 April 2017

Accepted after revision: 23 May 2017

Publication Date:
05 July 2017 (eFirst)

Published as part of the Cluster C–C Activation
Dedicated to Professor Teruaki Mukaiyama in celebration of his 90th birthday

Abstract

Formal [4+2] cycloaddition between 3-ethoxy-2-alkylcyclobutanones and nitrosobenzene proceeded by activation with Me3SiOTf to afford 6-alkyl-2-phenyl-2H-1,2-oxazin-5(6H)-one by regioselective cleavage of the more substituted C2–C3 bond of the cyclobutanone ring. On the other hand, reactions of 3-phenylcyclobutanones and 2-benzyloxycyclobutanone with nitrosobenzene gave γ,δ-unsaturated and cyclic hydroxamic acid derivatives, respectively, by cleavage of a cyclobutanone C1–C2 bond.

Supporting Information

 
  • References and Notes

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  • 26 6-tert-Butyl-2-phenyl-2H-1,2-oxazin 5(6H)-one (2a) – Typical Procedure To a stirred mixture of cyclobutanone 1a (143 mg, 0.84 mmol) and nitrosobenzene (30 mg, 0.28 mmol) in CH2Cl2 (2 mL) was added Me3SiOTf (0.17 mL, 0.92 mmol) at r.t. The reaction mixture was stirred for 10 min. The reaction was quenched by addition of potassium sodium tartrate. The mixture was extracted with EtOAc, and the organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by preparative thin-layer chromatography on silica gel (hexane/Et2O = 1:2) to afford 2a (43.6 mg, 0.19 mmol, 67%) as a brown solid; mp 69.0–70.0 °C. 1H NMR (600 MHz, CDCl3): δ = 1.16 (s, 9 H), 4.20 (s, 1 H), 5.34 (d, J = 7.2 Hz, 1 H), 7.14 (t, J = 7.5 Hz, 1 H), 7.22 (d, J = 8.4 Hz, 2 H), 7.40 (t, J = 8.1 Hz, 2 H), 7.71 (d, J = 7.8 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ = 26.7, 34.7, 91.2, 99.3, 114.5, 124.4, 129.5, 139.8, 140.6, 188.1. IR (CHCl3): 3018, 1576, 1223, 1209 cm–1. HRMS: m/z calcd for C14H18NO2: 232.13375; found: 232.13476.