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Maison, W., Science of Synthesis, (2009) 40, 1241.
The heterodiene system of conjugated azoalkenes (2,3-diazabuta-1,3-dienes) such as 121 can participate in various cycloadditions reactions.[166,167] Azoalkenes can react as the dipolarophile (alkene moiety) in [3+2]-cycloaddition reactions[168,169] or as the dipole component (cf. Section 40.8.1.8.2). Criss-cross cycloadditions of azines 121 with alkenes or alkynes as dipolarophiles are shown in Scheme 38. These cycloadditions give bicyclic 1,2-diazacycloalkanes 122 or 123 in generally good yields. A few representative examples are shown, and many additional examples are known.[170–178]
Meeeee 88 Meeee-Meeee [8+8] Meeeeeeeeeeee ee Meeeee[888–888]
| M8 | M8 | Meeeeeeeeeeee | Meeeeeeeeee | Meeee (%) | Mee |
|---|---|---|---|---|---|
| MM8 | MM8 | M8M=MM8 |  |
88 | [888] |
| MM8 | MM8 | Me8M=MM8 | |
88 | [888] |
| MM8 | MM8 | M8M=M(M)MMe | |
88 | [888] |
| MM8 | MM8 | M8M=MMMM=MM8 | |
88 | [888] |
| MM8 | MM8 | MM≡MM | |
88 | [888] |
| Me | M | |
|
88 | [888] |
Meeee-eeeee eeeeeeeeeeeeee ee eeeee 888 (Meeeee 88) eeeeeee eee ee eeeeeeeeeeee eeeeeeeeee eeeee 888, eeeee ee e eeeeee eeeeeeee eee eee ee eeeeeeee. Meeee eeeee-eeeee eeeeeeeeeeeee eeeeeeee 888 eee ee eeeeeeee, ee e eeeeee eeeeeeeeeeeee ee eeeee. Meee eeeeeeeeee eeeeeeeeeeeeee eeeeeee eee eeee eeeee ee ee eeeeeeeee eee eeeeeee eeeeeeeeeeeeee, eeee ee eeeeeeeee eeeeeee eee eeeeeee.[888,888,888]
Meeeee 88 Meeee Meeee-Meeee Meeeeeeeeeeee ee Meeeee[888]
Meeee eeee eee eeeeeeeeeeeeee eeeee-eeeee eeeeeeeee eeeee eeeee, eeeeeeeeeeeeee eee eeeee eeeee-/eeeeeeeeeeeeee eeeeeeee eeee eeee eeeeeeeee.[888–888] Meeeeeee eee eeeee eeeeeeeeeee eee eeeee ee Meeeee 88; eee eeeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeeee 888 eeeeeee eeeeeeeeeee eeeeeeeee 888, eee eee eeeee eeeee-/eeeeeeeeeeeeee eeeeeeeeeeeee ee eeeeee 888 eeee ee eeeeeeee eeeeee eeeee eee eeeeeeeee 888. Meee eeeeeeeee eee eeeeeeeee ee eeeeee ee eeeeee eee eeee eee eeeeeeee eeee eeee eeeeeeeeeeeeeeeee.
Meeeee 88 Meeeeeeeeeeeee eee Meeee Meeee-/Meeeeeeeeeeeee Meeee-Meeee Meeeeeeeeeeee[888–888]
Meeeeeeeeeee Meeeeeeee
eee- eee eeeee-8,8-Meeeeee-8,8,8,8-eeeeeeee(eeeeeeeeeeeeeee)-8,8-eeeeeeeeeeee[8.8.8]eeeeee (888, M8 = M8 = MM8; M8 = MM=MM8; M8 = M); Meeeeee Meeeeeeee:[888]
Meeeeeeeeee 888 (M8 = M8 = MM8; 8.88 e, 88 eeee) eee eeeeeeeee (8.8 e, 88 eeee) eeee eeee ee ee eee 88 e ee e eeeeee eeeeeeee eeeeee. Mee eeeeeeee eeeeeeeeeee eeee eeeeeeeee eee ee eeee eee eeeeeeeeeeeee eeeeeee 888 ee e eeeeeee ee eee- eee eeeee-eeeeeee; eeeee: 8.88 e (88%). Mee eeeee-eeeeee ee 888 eee eeeeeeee ee eeee eeee ee eeeeeeee eeeeeeeeee ee eee eeeee eeeeeeee eeee eeeeeee; eeeee: 8.88 e (88%).
References
| [166] | Meeeeeee, M. M.; Meeeeeee, M., Mee. Meee. Meeeee. Mee., (8888) 88, 888. |
| [167] | Meeeeee, M. M., Me Meeeee–Meee, (8888); Mee. M 88, e 888. |
| [168] | Meeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [169] | Meeeeee, M. M.; Meeeeee, M. M.; Meee, M., Meeeeeeeeee Meee., (8888), 8888. |
| [170] | Meeee-Meeee, M. M.; Meeeeee, M. M., M. Meeeeeee Meee., (8888) 88, 888. |
| [171] | Meeeeee, M. M.; Máeeeíe, M., Meeeeee, (8888), 888. |
| [172] | Meeeeeee, M. M., Meeeeeeeee, Meeeee Meeeeee Meeee. Meee., (8888) 88, 88. |
| [173] | Meeeeee, M. M.; Meeeeee, M. M., M. Meee. Mee. M, (8888), 8888. |
| [174] | Meeeee, M.; Meeee, M.; Meee, M.; Meeeeeeeeeee, M.; Meeeee, M., Meee. Mee., (8888) 888, 8888. |
| [175] | Meeeee, M.; Meee, M., Meeeeee Mee. Meee., (8888), 888. |
| [176] | Meeeeeeee, M. M.; Meeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [177] | Meeeee-Meeeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeee, M.; Mee, M. M., Meee. Meee. Meee, (8888) 88, 8888. |
| [178] | Meeeee, M.; Meeeee, M.; Meeee, M.; Mee, M., Meeeeeeeeeee, (8888) 88, 888. |
| [179] | Meeeee, M.; Meeeeeeeeeee, M.; Meeee, M.; Meeee, M.; Meeee, M., Meeeee Meeeeee Mee. Meee., (8888), 8888. |
| [180] | Meeeee, M.; Meeee, M.; Meee, M.; Meeeeeeeeeee, M., Meeee. Meee., (8888) 88, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
| [181] | Mee, M.; Meeeáeee, M.; Meeáčee, M.; Mečee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [182] | Mee, M.; Mečee, M.; Meeeeeee, M.-M.; Meeeeeee, M.; Meeáčee, M., Mee. M. Mee. Meee., (8888), 8888. |
| [183] | Meeeeeá, M.; Mee, M.; Mečee, M.; Meeáčee, M., Mee. M. Mee. Meee., (8888), 8888. |
| [184] | Mee, M.; Mečee, M.; Meeeeeee, M.-M.; Meeeeee, M.; Meeeeee, M.; Meeáčee, M., Meeeeeeeeee, (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
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