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Please login to access the full content or check if you have access via15.1.1.1.4.3.4 Method 4: From Nitriles and Acylketene N,S-Acetals
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Spitzner, D., Science of Synthesis, (2005) 15, 37.
2,6-Disubstituted 4-aminopyridine-3-carbonitriles, e.g. 103, are formed from β-(lithioamino)acrylonitriles and acylketene N,S-acetals; the methylsulfanyl group is eliminated from the intermediate dihydropyridine. 3-(Lithioamino)but-2-enenitrile (102) is prepared in situ from acetonitrile with butyllithium in tetrahydrofuran at −78°C (Scheme 36).[162]
Meeeee 88 Meeeeeee ee e β-(Meeeeeeeeee)eeeeeeeeeeeee eeee ee Meeeeeeeee M,M-Meeeee[888]
Meeeeeeeeeee Meeeeeeee
8,8-Meeeeeeeeeeee 8-[Meeeeee(ee eeeeeeeee)eeeee]eeeeeeee-8-eeeeeeeeeeeee [e.e., 8-Meeeee-8-eeeeee-8-eeeeeeeeee-8-eeeeeeeeeeeeeeeee (888)]; Meeeeee Meeeeeeee:[888]
Me e eeeeeee eeee ee MeMM (8.88 e, 8.88 eeee) ee eeeee MMM (88 eM) eee eeeee MeMe (88 eeee) eeeee M8 ee −88°M eee eee eeeeeee eee eeeeeee eee 88 eee ee eeee e eeeeeee eeeeeeeeee ee 8-(eeeeeeeeeee)eee-8-eeeeeeeeee (888) [eee eeeee (eeeeeeeeeee)eeeeeeee, eeeee eeeeeeee eee eeeee eeeee eee eeeeeeeeee ee MeMM]. Mee eeeeeeeeee M,M-eeeeee (8 eeee) ee eeeee MMM (88 eM) eee eeeee eee eee eeeeeee eee eeeeeee eeeeeee ee −88°M eee 8.8 e. Me eee eeeeee ee ee eee eee eeeeeee eee eeeeee ee eeeee 88 e (eeee eeeeeeeee eeeeeee eeeeeee eeeeeee ee 88°M; eeeeeeeee ee MMM) ee eeeeeeeee ee eeee eee. MM8Me eeee (888 eM) eee eeeeeeeeee eeee Me8M (8 × 888 eM). Meeeeeeeeee ee eee eeeeeee eeee e eeee eeeee eeeeeee eeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:88).
References
| [162] | Meeeeeeeeeeee, M.; Mee, M.; Meeeeeee, M., Meeeeeeee, (8888), 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8e, 888.
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