# Natural Product-Oriented Photo-Induced Deintrogenative Annulations of 1-Alkenylbenzotriazoles
## 3 Materials and Methods
### General Procedure
117-118 \({}^{\circ}\)C; \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)) 847.6, 37.9, 37.7, 36.5, 36.0, 30.2, 24.3, 24.1, 19.6. HRMS m/ z calcd for C\({}_{18}\)H\({}_{22}\)N\({}_{3}\)O\({}_{2}\) [M+H]\({}^{+}\): 312.1712; found: 312.1708. (4b\({}^{7}\)R,8a\({}^{7}\)R)-6\({}^{,}\)7\({}^{,}\)D-Dihydro-5\({}^{,}\)H,9\({}^{,}\)H-spiro[cyclopentane-1,8\({}^{,}\)-[8a,4b](epoxyethano)carbazol]-11\({}^{,}\)-one (**17g**): white solid; Yield: 64%; \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)) \(\delta\) 1.37-1.79 (m, 12H), 1.90-2.13 (m, 2H), 2.88 (d, \(J\) = 2.9 Hz, 2H), 4.83 (s, 1H), 6.71 (d, \(J\) = 7.8 Hz, 1H), 6.83 (t, \(J\) = 7.4 Hz, 1H), 7.05 (d, \(J\) = 7.4 Hz, 1H), 7.11 (t, \(J\) = 7.7 Hz, 1H). 1\({}^{3}\)C NMR (100 MHz, CDCl\({}_{3}\)) \(\delta\) 175.0, 145.6, 135.8, 128.7, 122.8, 120.5, 110.2, 51.6, 48.9, 40.1, 36.1, 33.5, 32.4, 25.3, 23.1, 17.3. HRMS m/ z calcd for C\({}_{18}\)H\({}_{22}\)NO\({}_{2}\) [M+H]\({}^{+}\): 284.1651; found: 284.1656. 3-(1H-Benzo[d][1,2,3]triazol-1-yl)-2-(2-(methoxymethoxy)ethyl)-4,4-dimethylcyclohex-2-en-1-one **(15h)**: light yellow oil; Yield: 72%; \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)) \(\delta\) 0.95 (s, 3H), 1.39 (s, 3H), 1.92 (ddd, \(J\) = 13.3, 7.6, 5.8 Hz, 1H), 2.09-2.25 (m, 3H), 2.67-2.87 (m, 2H), 3.09 (s, 3H), 3.21-3.37 (m, 2H), 4.28-4.35 (m, 2H), 7.36-7.44 (m, 2H), 7.52 (ddd, \(J\) = 8.1, 7.0, 1.1 Hz, 1H), 8.11 (dt, \(J\) = 8.4, 1.0 Hz, 1H). \({}^{3}\)C NMR (100 MHz, CDCl\({}_{3}\)) \(\delta\) 198.1, 156.8, 145.2, 136.0, 134.0, 128.4, 124.3, 120.3, 110.4, 95.9, 65.3, 55.1, 38.0, 37.1, 34.7, 27.0, 26.3, 26.1. HRMS m/ z calcd for C\({}_{18}\)H\({}_{24}\)N\({}_{3}\)O\({}_{3}\) [M+H]\({}^{+}\): 330.1805. 10-(2-(Methoxymethyl)-9,9-dimethyl-8,9-dihydropyprojud[1,2-a]indol-6(7H)-one **(20h)**: colorless oil; Yield: 42%; \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)) \(\delta\) 1.53 (s, 6H), 1.95 (t, \(J\) = 6.6 Hz, 2H), 2.81 (dd, \(J\) = 7.1, 6.2 Hz, 2H), 3.16 (dd, \(J\) = 8.2, 7.2 Hz, 2H), 3.36 (s, 3H), 3.78 (dd, \(J\) = 8.3, 7.2 Hz, 2H), 4.65 (s, 2H), 7.26-7.34 (m, 2H), 7.46-7.52 (m, 1H), 8.47-8.53 (m, 1H). \({}^{3}\)C NMR (100 MHz, CDCl\({}_{3}\)) \(\delta\) 169.5, 141.3, 134.5, 131.1, 124.8, 123.9, 118.0, 116.8, 113.6, 96.6, 67.3, 55.4, 37.0, 32.7, 30.9, 28.6, 25.7. HRMS m/ z calcd for C\({}_{18}\)H\({}_{24}\)NO\({}_{3}\) [M+H]\({}^{+}\): 302.1756; found: 302.1751. 6-(1H-Benzo[d][1,2,3]triazol-1-yl)-7-(2-(methoxymethoxy)ethyl)spiro[4.5]dec-6-en-8-one **(15i)**: light yellow oil; Yield: 74%; \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)) \(\delta\) 1.20-1.28 (m, 2H), 1.39-1.63 (m, 4H), 1.81-1.99 (m, 2H), 2.10-2.22 (m, 3H), 2.31-2.42 (m, 1H), 2.65-2.81 (m, 2H), 3.08 (s, 3H), 3.22-3.34 (m, 2H), 4.26-4.34 (m, 2H), 7.35-7.44 (m, 2H), 7.53 (ddd, \(J\) = 8.1, 7.0, 1.0 Hz, 1H), 8.11 (dt, \(J\) = 8.3, 1.0 Hz, 1H). \({}^{3}\)C NMR (100 MHz, CDCl\({}_{3}\)) \(\delta\) 198.3, 155.9, 145.2, 136.5, 134.3, 128.5, 124.4, 120.3, 110.3, 95.8, 65.4, 55.1, 48.7, 36.9, 35.2, 34.6, 33.9, 26.5, 24.5, 24.3. HRMS m/ z calcd for C\({}_{20}\)H\({}_{26}\)N\({}_{3}\)O\({}_{3}\) [M+H]\({}^{+}\): 356.1974; found: 356.1961. 10\({}^{-}\)(-(2-(Methoxymethyl)-)-7\({}^{,}\)8-dihydroxy-ro-6\({}^{,}\)H-spiro[cyclopenta-1,9\({}^{,}\)-pyrid[1,2-a]indol]-6\({}^{,}\)-one **(20i)**: light yellow oil; Yield: 35%; \({}^{1}\)H NMR (400 MHz, CDCl\({}_{3}\)) \(\delta\) 1.79-1.96 (m, 6H), 1.99 (dd, \(J\) = 7.1, 6.0 Hz, 2H), 2.15-2.29 (m, 2H), 2.76 (dd, \(J\) = 7.1, 5.9 Hz, 2H), 3.10 (dd, \(J\) = 8.3, 7.2 Hz, 2H), 3.36 (s, 3H), 3.81 (dd, \(J\) = 8.3, 7.2 Hz, 2H), 4.65 (s, 2H), 7.23-7.32 (m, 2H), 7.46-7.51 (m, 1H), 8.46-8.52 (m, 1H). \({}^{3}\)C NMR (100 MHz, CDCl\({}_{3}\)) \(\delta\) 169.7, 141.9, 134.5, 131.1, 124.6, 123.8, 118.0, 116.8, 112.8, 96.5, 67.0, 55.3, 43.4, 39.3, 34.5, 31.7, 25.7, 25.6. HRMS m/ z calcd for C\({}_{20}\)H\({}_{26}\)NO\({}_{3}\) [M+H]\({}^{+}\): 328.1913; found: 328.1909.