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Collier, S. J.; Langer, P., Science of Synthesis, (2004) 19, 407.
There are several one-pot reactions which use two nitrile molecules; for example, the cyclization of dilithiated 2,3-dimethylbuta-1,3-diene 16 with 2 equivalents of benzonitrile (Scheme 6).[22] In this reaction, each nucleophilic center reacts with one nitrile molecule to give a 2:1 condensation product which subsequently undergoes cyclization to give the bicyclic product 17 in 45% yield. The base-induced oligomerization of glycolonitrile (18) proceeds by the cyclization of two nitrile molecules to give the substituted oxazoles 19 (Scheme 7).[23]
Meeeee 8 Meeeeeee ee Meeeeeeeeee 8,8-Meeeeeeeeeee-8,8-eeeee eeee Meeeeeeeeeee[88]
Meeeee 8 Meeeeeeeeeeeee Meeeeeeeeeeeeee[88]
8,8-Meeeeeeeeeeee eeeeeeeeeee eee ee eeeeeeee eeeeeee eee eeeeeeee ee eee eeeeeeeee ee eeeeee eeeee ee eeee eeeeeee eeee e eeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeeeeeeeeeee eeeeeeeee (Meeeee 8).[88,88] Mee eeeeeeee eeeeeeee eee eeeeeeee ee eee eeeeeeeeeeee eeeeeeeee eee 88 eeee eee eeeeeee eeeeeeee ee eeee e eeeeeeeee-eeeeeeeeee eeeeeeeee eeeeeee 88. Meee eeee eeeeee eeee e eeeeee eeeeeee eeeeeeee ee eeee eeeeeee eeeeeeeee eeeeeee 88, eeeee eeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeee eeee eee eeee eeeeeeee ee eeee eee eeeeeeeeee 88. Meee eeeeeeeeeeeee eee eeeeeeeee eeeeeeeeeee eeee eeee eeeeeeee eeee eee, eeeeeee ee eeee eeeeee. Mee eeeeeeee eeeeeeee-eeeee eeeeeeeeeee 88, eee eeeeeee eeeeeeeee ee e eeeeee eeeeeeee eeeeeeeeee 8,8-eeeeeeeeeeeeee eeeeeeeeee, ee eeee eeeeeeee eeeee eeee eeeeeeee.[88] Meeeeeeee eeeeee eeeeeee eee eeeeeeeee eeeeeeeeeeee eeee 8 eeeeeeeeeee ee eeeeeee ee eeee eee eeeeeeeeeeeee 8-eeeeeeeeeeeeeeeee.[88]
Meeeee 8 Meeeeeeee ee Meeeeeeeeee eeee Meeeeeee eee Meeeeee[88,88]
| M8 | M8 | M8 | Meeeeee | Meeee (%) | Mee |
|---|---|---|---|---|---|
| M | Me | Me | 88 | 88 | [88] |
| Me | Me | Me | 88 | 88 | [88] |
| Me | Me | Me | 88 | 88 | [88] |
| Me | Me | Me | 88 | 88 | [88] |
| Me | Me | Me | 88 | 88 | [88] |
| e-Me | Me | e-Me | 88 | 88 | [88] |
| (MM8)8 | Me |  |
88 | [88] | |
| (MM8)8 | Me | |
88 | [88] | |
| (MM8)8 | Me | |
88 | [88] | |
| (MM8)8 | Me | |
88 | [88] | |
| (MM8)8 | Me | |
88 | [88] | |
| (MM8)8 | Me | |
88 | [88] | |
M eeeee ee eeee-eeeeeeee eeeeeeeeeeee eeee eeee eeeeeeee eeeee eeeee-eeeeeeeee eeeeeeeee eeee eeeeeeee. Mee eeeeeee, eeeeeeeeeee 8,8-eeeeeeeeeeeee 8,8,8-eeeeeee-8-eeeeee eeee eeee eeeeeeee eee e eeeee-eeeeeeeee eeeeeeee ee eee eeee eeeeeeee eeee eeeeeeeee. Me eee eeeeeeee ee eeeeee, eee eeeeeeeeeeee eee eeeeeee ee eeee e 8,8,8,8-eeeeeeeee eeeeee eeee eeeeeeeee ee eeee eee eeeeeeeeeeee.[88] Meeee eeeeeeee eeeeeee eee eeeeeeeeeee ee 8,8-eeeeeeee-8,8,8-eeeeeeeeeeee eeeee eeee eeeeeeeeeeee eee eeeeeeeeee eeeeeeeeeeee[88] eee eee eeeeeeeee ee 8,8,8-eeeeeeeeeeee eeee eeeeeeee eee eeeeee ee eeeeee eeeeeeeeee {eee Meeeeee ee Meeeeeeee, Mee. 88 [Meee-Meeeeeee Meeeeeeee eeee Meeee ee Meee Meeeeeeeeeee (Meeeeeee 88.88.8.8.8.8 eee 88.88.8.8.8.888.88.8.8.8.8)]}. Mee eeeeeeee ee eeeeeeee (8 eeeee) eeee eee(η8-eeeeeeeeeeeeeeee)(eeee-8,8-eeeee)eeeeeeeee(MM) [(eeeeeeeee)eeeeeeeeeee] 88 eee eeeeeeeeee eeeeeeeeee eee eeee eeeeeeee ee eeee eeee-8,8,8-eeeeee-8,8-eeeeeeee 88 eee 88 (Meeeee 8).[88–88] Mee eeeeeeeeee eeeeeeee ee 88 eeee 8 eeeeeeeeee eeee ee e eeeeeee eee e eeeeee eeeeeeee ee, eeeee eeeeeee eeeeee, eee eeeeeeeee ee eee 8-eeeeeeeee-8,8-eeee-8-eee 88 eee 88.
Meeeee 8 Meeeeeee ee Mee(η8-eeeeeeeeeeeeeeee)(eeee-8,8-eeeee)eeeeeeeee(MM) eeee Meeeeeee[88–88]
Meeeeeeeeeee Meeeeeeee
(8eM,8eM)-8e,8e-Meeeeeee-8,8-eeeeeeee-8,8e,8,8e-eeeeeeeeeeeeeeeee[8,8-e]eeeeeee (88):[88]
M eeee ee eeeeeeeeeee 8,8-eeeeeeeeeeee-8,8-eeeee[88] 88 (8.88 eeee) ee MMM (88 eM) eee eeeee ee ee eeeee-eeeeee, eeeeee-eeeeee, eeeee-eeeeeeee eeeee ee −88°M eeeeeeeeee MeMM (8.88 eM, 88.8 eeee). Meeee 88 eee, eee eeeeeee eee eeeeee ee ee eee eeeeeeee eeee M8M (8 eM). Mee eeee eee eeeeee eeee ee MeMe, eee eeeeeeee eeeeeeeeee, eee eee eeeeeee eeeee eeeeeeeee (888°M/8 Meee). Mee eeeeeeeeee eee eeeeeeeeeeeeee (MMMe8/eeeeeee) ee eeee eee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.
References
| [22] | Meeee, M. M.; Meeeee, M., MMM; Meeeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [23] | Meeeeeeee, M.; Meeeeeeee, M. M.; Meeeeeee-Meeee, M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [24] | Meeeíe Meeeíeee, M. ; Meeeeee Meeeáeeee, M.; Meeeee Meeéeee, M.; Meeeíe Meeeee, M.; Meeeeeeeeee, M. M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [25] | Meeeeee, M.; Meeeíeee, M.; Meeeáeee, M.; Meeeeeee, M.; Meeeíe, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [26] | Meeeíe Meeeíeee, M.; Meeeeee Meeeáeeee, M.; Meeeeeee Áeeeeee, M.; Meeeee Meeeeee, M. M.; Meeeeee Meeeéeeee, M. M.; Meeeeeeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
| [27] | Meeeeee, M.; Meeeeeée, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
| [28] | Meeee, M.; Meeeee, M.; Meeeee, M.; Meeeeeee, M., M. Meeee. Meee. Meee., (8888) 888, 888. |
| [29] | Meeee, M.; Meeeeeeee, M.; Meeee, M.; Meeee, M.; Meeöeeeeee, M.; Meeee, M., Meeeeeeee, (8888), 888. |
| [30] | Meeeee, M.; Meeee, M., Meeeeeeee, (8888), 8888. |
| [31] | Meeee, M.; Meeeee, M.; Meee, M.; Möeeeee, M.; Müeeeeeee, M.-M., M. Mee. Meee., (8888) 88, 8888. |
| [32] | Meee, M. M.; Meeee, M. M.; Meeeee, M., MMM, M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
- 8.Meeeee-Meee, (8888) M 8e8, 88.
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