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Volumn , Issue 8, 2008, Pages 1222-1224

Intramolecular cycloaddition in cyclohexa-2,4-dienone and photochemical reactions: An efficient route to azatriquinane and azasterpurane frameworks

(3) Singh, Vishwakarma a Sahu, Bharat C a Mobin, Shaikh M a

a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY (India)

Author keywords

1,3 acyl shift photochemistry; Cycloaddition; Cyclohexa 2,4 dienone; Oxa di methane rearrangement

Indexed keywords

ANTINEOPLASTIC AGENT; AZASTERPURANE; AZATRIQUINANE; CYCLOHEXA 2,4 DIENONE; CYCLOHEXANE DERIVATIVE; NITROGEN;

ARTICLE; CRYSTAL STRUCTURE; CYCLOADDITION; DECARBOXYLATION; DEOXYGENATION; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PHOTOCHEMISTRY; PHOTOREACTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 44349186657 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072588 Document Type: Article

Times cited : (9)

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- All the compounds gave satisfactory spectral and analytical data. Data for adduct 13: mp 159-161°C IR: 1733 cm-1. 1H NMR (300 MHz, CDCl3, δ, 7.70-7.74 (m, 2 H, 7.31-7.37 (m, 2 H, 5.20-5.24 (br m, 1 H, β-H of β,γ-enone moiety, 3.60-3.68 (m merged with part of an AB system, JAB, 10.6 Hz, 2 H, 3.52 (part of an AB system, JAB, 10.6 Hz, 1 H, 3.14 (part of an AB system, JAB, 6.0 Hz, 1 H, 2.85-2.92 (m merged with another signal, 1 H, 2.84 (part of an AB system, JAB, 6.0 Hz, 1 H, 2.45 (s, 3 H, Me, 2.12-2.34 (m, 3 H, 1.87 (d, J, 1.5 Hz, 3 H, Me, 1.26 (ddd, J1, 12.1 Hz, J2, 5.1 Hz, J3, 1.8 Hz, 1 H, 13C NMR (75 MHz, CDCl 3, δ, 200.9 (CO, 146.4, 143.8, 133.9, 129.8, 127.3, 121.6, 58.8, 56.6, 52.0, 51.8, 49.2, 44.6, 41.5, 24.8, 21.5, 20.2. HRMS ESI
- 4: 360.1270; found: 360.1274.

45
- 44349111512
- Data of the compound 15: mp 164-166°C IR: 1723 cm -1. 1H NMR (400 MHz, CDCl3, δ, 7.73 (d, J, 8.0 Hz, 2 H, 7.34 (d, J, 8.0 Hz, 2 H, 5.00 (br m, 1 H, β-H of β,γ-enone moiety, 3.60-3.64 (m, 2 H, 3.44 (d, J, 10.3 Hz, 1 H, 2.71-2.79 (m, 2 H, 2.44 (s, 3 H, 1.83-2.18 (m, 4 H, 1.79 (d, J, 1.8 Hz, 3 H, 1.16-1.21 (m of dd, J1, 12.5 Hz, J2, 5.8 Hz, 1 H, 13C NMR (100 MHz, CDCl 3, δ, 207.6 (CO, 148.7, 143.6, 134.3, 129.9, 127.5, 120.2, 59.3, 52.4, 49.6, 40.6, 38.9, 37.9, 28.0, 21.7, 19.8. HRMS (ESI, m/z [M, H, calcd for C18H21SNO3: 332.1320; found: 332.1306. Crystal data: C18H21NO 3S, M, 331.42, crystal size, 0.23 x 0.18 x 0.15 mm, monoclinic, P21/n, Z, 4, a, 11.4521(8, b, 10.57697, c, 13.7
- 2 = 0.1161. The complete crystal data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cifquoting the CCDC number 677807.

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50
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- Singh, V.¹

51
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52
- 44349189572
- Data for compound 18: IR: 1726 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.61 (d, J, 8.0 Hz, 2 H, ArH, 7.29 (d, J, 8.0 Hz, 2 H, 3.22-3.27 (m, 2 H, 2.94 (superimposed dd, J 1, 9.0 Hz, 1 H, 2.78 (d, J, 9.7 Hz, 1 H, 2.64 (dd, J1, 9.7 Hz, J2, 5.2 Hz, 1 H, 2.50 (dd, J1, 18.3 Hz, J2, 10.0 Hz, 1 H, 2.27-2.46 (s merged with a m, 4 H, 1.86-1.89 (m, 1 H, 1.69-1.80 (m, 2 H, 1.34 (s, 3 H, 1.18-1.21 (br m, 1 H, 13C NMR (100 MHz, CDCl 3, δ, 213.9, 144.2, 131.5, 129.9, 128.2, 53.1, 48.7, 48.6, 46.7, 46.0, 45.5, 45.4, 45.2, 41.8, 21.7, 13.5. HRMS ESI, m/z [M, H, calcd for C18H21SNO3: 332.1320; found: 332.1309
- 3: 332.1320; found: 332.1309.

53
- 44349134801
- Data for compound 19: mp 132-134°C. IR: 1772 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.72 (d, J, 8.0 Hz, 2 H, 7.34 (d, J, 8.0 Hz, 2 H, 5.29 (br s, 1 H, 4.06 (m of d, J, 14.3 Hz, 1 H, 3.89 (superimposed dd, J1, J2, 8.0 Hz, 1 H, 3.74 (m of d, J, 14.3 Hz, 1 H, 2.95 (dd, J1, 17.7 Hz, J2, 9.1 Hz, 1 H, 2.67-2.74 (m, 2 H, 2.50-2.58 (m, 1 H, 2.44 (s, 3 H, Me, 2.34-2.42 (m, 1 H, 2.00 (ddd, J1, 12.3 Hz, J2, 6.1 Hz, J3, 2.4Hz, 1 H, 1.22(s, 3 H, 1.00-1.07 (m, 1 H, 13C NMR (100 MHz, CDCl3, δ, 208.8, 143.8, 139.8, 133.4, 129.9, 127.8, 118.7, 63.1, 53.7, 51.4, 46.1, 33.9, 30.8, 23.8, 21.7, 20.3. HRMS ESI, m/z [M, Na, calcd for C18H 21SNO3Na: 354.1140; found: 354.1143
- 3Na: 354.1140; found: 354.1143.

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