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Synlett 2014; 25(3): 385-388
DOI: 10.1055/s-0033-1340310
DOI: 10.1055/s-0033-1340310
letter
Synthesis of Novel Benzo[6,7][1,4]oxazepino[4,5-a]quinazolinone Derivatives via Transition-Metal-Free Intramolecular Hydroamination
Authors
Further Information
Publication History
Received: 10 October 2013
Accepted after revision: 01 November 2013
Publication Date:
06 December 2013 (online)
Abstract
Novel benzo[6,7][1,4]oxazepino[4,5-a]quinazolinone derivatives were synthesized through an efficient 7-exo-dig hydroamination of 3-substituted-2-[2-(prop-2-yn-1-yloxy)phenyl]-2,3-dihydroquinazolin-4(1H)-ones in the presence of potassium tert-butoxide (KOt-Bu) in DMF at 130 °C.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information (PDF)
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- 27 Synthesis of Benzo[6,7][1,4]oxazepino[4,5-a]quinazolinone Derivatives 2 – General Procedure A mixture of 3-substituted 2-[2-(prop-2-yn-1-yloxy)phenyl]-2,3-dihydroquinazolin-4(1H)-one 1 (1 mmol) and KOt-Bu (2 mmol) in DMF (5 mL) was stirred at 130 °C for 3–4 h. Upon completion of reaction, checked by TLC, the reaction mixture was poured into cold H2O, the precipitate was filtered off, and the residue was purified using plate chromatography eluting with PE–EtOAc (4:1). 8-Butyl-1-methyl-7b,8-dihydro-9H-benzo[6,7][1,4]-oxazepino[4,5-a]quinazolin-9-one (2a) Yield 0.23 g (68%); yellow oil. IR (KBr): 3060, 2957, 2850, 1659 (C=O), 1614, 1482 cm–1. 1H NMR (400 MHz, DMSO-d 6): δ = 0.87 (t, J = 7.2 Hz, 3 H, NCH2CH2CH2CH 3), 1.27–1.33 (m, 2 H, NCH2CH2CH 2CH3), 1.54–1.63 (m, 2 H, NCH2CH 2CH2CH3), 2.02 (s, 3 H, CH3), 2.84–2.91 (m, 1 H, NCH 2aCH2CH2CH3), 4.04 (m, 1 H, NCH 2bCH2CH2CH3), 5.76 (s, 1 H, CH, H2), 6.67 (s, 1 H, CH), 6.72 (d, J = 7.6 Hz, 1 H, H13), 6.82 (t, J = 7.6 Hz, 1 H, H11), 6.88 (d, J = 7.0 Hz, 1 H, H4), 6.99 (t, J = 7.0 Hz, 1 H, H6), 7.05 (d, J = 7.0 Hz, 1 H, H7), 7.24 (dt, J = 7.0, 1.2 Hz, 1 H, H5), 7.29 (dt, J = 7.6, 1.2 Hz, 1 H, H12), 7.77 (dd, J = 7.6, 1.2 Hz, 1 H, H10). 13C NMR (100 MHz, DMSO-d 6): δ = 14.1, 20.0, 20.3, 30.3, 45.3, 70.6, 107.1, 113.7, 115.9, 119.4, 121.2, 123.9, 124.9, 128.3, 130.5, 131.2, 134.1, 143.5, 143.7, 155.1, 162.0. Anal. Calcd for C21H22N2O2: C, 75.42; H, 6.63; N, 8.38. Found: C, 75.28; H, 6.78; N, 8.19. Data for compounds 2b–i are given in the Supporting Information.