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Rademacher, P., Science of Synthesis, (2009) 40, 1163.
The carbonyl groups of hydrazides (acylhydrazines and diacylhydrazines) can be reduced to methylene groups, providing alkyl-substituted hydrazines. Complex metal hydrides such as lithium aluminum hydride or diborane are generally utilized as reagents. The former reagent will reduce simultaneously an acyl and a hydrazone group {see Section 40.7.1.1.4.2; cf. Science of Synthesis, Vol. 21 [Three Carbon—Heteroatom Bonds: Amides and Derivatives; Peptides; Lactams (Section 21.13.16)]}. This method is particularly useful for the synthesis of cyclic or bicyclic hydrazine derivatives, such as 2,2,6,6-tetramethyltetrahydropyrazolo[1,2-a]pyrazole (102), which is obtained in excellent yield from 2,2,6,6-tetramethyltetrahydropyrazolo[1,2-a]pyrazole-1,5-dione (101) with a large excess of the reducing agent (Scheme 47).[118] For details see Section 40.8; see also Houben–Weyl, Vol. E 16a.[9]
Meeeee 88 Meeeeeeee ee e Meeeeeee Meeeeeeee Me Meee e Meeeeeee Meeeeeeee[888]
Me eeeeeeeee eeee eeeeeee eeeeeeee eeeeeee ee eeeeee, eeeeeeeeee 888 eeeeeeee eeeeee eee eeeeeeeeeeeee eeeee eeeeeeeeeee 888 (Meeeee 88).[88,88,888–888]
Meeeee 88 Meeeeeeee ee Meeeeeeeee Me Meee Meeeeeeeee[88,88,888–888]
M8 | M8 | M8 | M8 | Meeeeeeeee | Meeeee (%) | Mee |
---|---|---|---|---|---|---|
M | 8-M8MM8M8MM8 | Me | M | MMM, MMM | 88 | [888,888] |
Me | Me | Me | Me | MeMeM8, Me8M | e.e. | [888] |
Me | Me | Me | Me | MeMeM8, Me8M | e.e. | [888] |
Me | Me | Me | Me | MeMeM8, Me8M | e.e. | [888] |
Me | Me | M | M | MeMeM8, MMM, eeeeee, 8 e | 88 | [88,888,888] |
8-M8MM8M8 | Me | Me | M | MeMeM8, MMM, eeeeee, 8 e | 88 | [888] |
8-eeeeeeeee | Me | M | M | MeMeM8 | 88 | [88] |
e e.e. = eee eeeeeeee.
Meeeeeeee ee 8-eeee-8-eeeeeeeeeeeeeee eeee eeeeeee eeeeeeee eeeeeee eeeeee ee eeeeeeeee eeee ee 8,8-eeeeeeeeeeeeeeeee, eee eeee eeeeeeeeee eee eee eeeeee eeee ee eeee eeeee ee eee eeeeeeeee ee eeeeeee. 8,8-Meeeeeeeee eeeeeeeee 888, eeeeeeeee eeeee eeee eeeeeeeee eeee eeeeee,[8] eee eeee eeeeee eeeeeeee eee eee ee eeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeee 888 (Meeeee 88).[888,888]
Meeeee 88 Meeeeeeee ee 8,8-Meeeeeeeeeee ee 8,8-Meeeeeeeeeeeeeeee[888,888]
M8 | M8 | Meeeee | Meeee (%) | Mee |
---|---|---|---|---|
M | Me | M | 88 | [888] |
Me | M | M | 88 | [888] |
Me | M | M | 88 | [888] |
Me | M | M | 88 | [888] |
Me | Me | M | 88 | [888] |
Me | Me | M | 88 | [888] |
Me | Me | M | 88 | [888] |
Me | Me | M | 88 | [888] |
Meeeeeeeeeeeee eeeeeeeeee eee ee eeeeeeeeeee ee eee eeeeeeeee ee eeeeeeeeee,[88] eeeeeeee e eeeeeeee 8,8-eeeeeeeeeeeee eeeeeeeee ee eeeeeeeee ee e eeeeeeeee eeee eee ee eeeeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeee. Mee eee eeeeeeeee ee eeee eeeeeeeee, eeeeeee eeeeeeee eee eeeeeeeee, eeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeeeee eeeeeeeeeee. Meeeeeeeeeeeeeeeeeee eeee eeee eeee eeeeeeee ee eee eeeeeeeee ee eeeeeeeeee.
Me eee eeeeeeeee ee eeeeeeeee ee ee eeeeeeeeeeeeee eeeee, ee ee eeeeeeeee 888, e eeeeee eeeee ee eeeeeeeee ee eeeeeeeee eeee eeeeeee eeeeeeee eeeeeee ee eeeeee eee eeeeeeeeee 888 (Meeeee 88).[888,888] Meee eeeeee eee eeee eeee ee eeeeeeeeee eeee eeeeeeeeeeee eeeeeeeeee e eeeeeeeee eeee, e.e. eee eee eeeeeeeeeee ee 8-eeeeeeeeeeeeeeeeeeeeeeeee [888, M8 = M; M8,M8 = (MM8)8].
Meeeee 88 Meeeeeeee ee Meeeeeeeee Meeeeeeee ee ee Meeeeeeeeeeeee Meeee eeee Meeeeee Meeeeeee Meeeeee[888,888]
Meeeeeeeeeee Meeeeeeee
8,8-Meeeeeeeeeeeeeeee (888, M8 = Me; M8 = M); Meeeeee Meeeeeeee eee 8,8-Meeeeeeeeeeee Meeeeeeeee:[888]
Me 8,8-eeeeeeeeeeeeeeeeeeee (888, M8 = Me; M8 = M; 8.88 e, 88.8 eeee) ee MMM (888 eM) ee 8°M eee eeeee e 8.88 M eeee ee eeeeee ee MMM (88 eM, 888 eeee ee MM8). Mee eeeeeee eee eeeeeee ee 8–8°M eee 88 eee, eeeeeee ee eeeeee ee, eee eeee eeeeee ee 888°M eee 88 e. Mee MMM eee MMM eeee eeeeeee eeeee eeeeeee eeeeeeee, eee eeeeeee eee eeeeeeeeee eeee 88% ee MMe (88 eM) ee 8°M, eeee eeeeeeee eee 8 e eee eeeeeeee eeee MeMM. Mee eeeeeee eee eeeeeeeee eeee Me8M, eee eeeeeee eee eeeee (MeMM8) eee eeeeeeee, eee eee Me8M eee eeeeeee. Meeeeeeeeeee ee eee eeeeeee eeee eee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.
8,8-Meeeeeee-8,8-eeeeeeeeeeeeeeeee (888, M8 = Me; M8 = Me); Meeeeee Meeeeeeee eee Meeeeeeeeeeeeeee Meeeeeeeee:[888]
Me 8,8-eeeeeeee-8,8-eeeeeeeeeeeeeeeeeeee (888, M8 = Me; M8 = Me; 8.88 e, 88.8 eeee) ee MMM (888 eM) ee 8°M eee eeeee, ee eeeee ee e eeeeeee, e 8.88 M eeee ee eeeeee ee MMM (88 eM, 888 eeee ee MM8). Mee eeeeeee eee eeeeeee ee 8–8°M eee 88 eee, eeeeeee ee eeeeee ee, eee eeee eeeeeeee eee 88 e. Mee eeeeeee eee eeeeeeee ee 8°M, eeeeeeeeee ee eeeeee 88% ee MMe (88 eM) eeeeeeee, eee eeee eeeeeeee eee 8 e. Mee eeeeeee eee eeeeeeee eeee eeeee MeMM eee eeeeeeeee eeee Me8M; eee eeeeeee eee eeeee (MeMM8), eee Me8M eee eeeeeee, eee eee eeeeeee eee eeeeeeeee ee eeee eee eeeeeeeee. Mee eeeee eeeeeeee eee eee eeeeeee eeeeeee; eeeee: 8.88 e (88%); ee 88–88°M/8.88 eMe.
References
[4] | Meeeeeeeee, M., Meee. Mee. Mee., (8888) 88, 888. |
[9] | Müeeee, M., Me Meeeee–Meee, (8888); Mee. M 88e, e 888. |
[15] | Meeeee, M. M.; Meeeeeeee, M. M.; MeMeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[16] | Meeeee, M.-M.; Meeee, M.; Meeeeeee, M.; Meeeee, M., MM 8 888, (8888); Meee. Meeee., (8888) 88, 88888. |
[49] | Meeeeeeeee, M. M.; Meeeee, M. M. M., Me Meeeeeeeeeeee Meeeeee Meeeeeeeee Meeee Meeeeeeeeeeeeee, Meeeeeeee, M. M.; Meee-Meee, M.; Meee, M. M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8, ee 888-888. |
[106] | Meeee, M. M.; Meeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[118] | Meeeeeee, M.; Meeeeeeeee, M., Meee. Mee., (8888) 888, 8888. |
[119] | Meeeee, M. M.; Meeeeee, M. M.; Meeeeeeee, M. M., Mee. Meee. Meeeee. Mee., (8888) 8, 888. |
[120] | Meeeee, M. M., MM 8 888 888, (8888); Meee. Meeee., (8888) 88, 88888. |
[121] | Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[122] | Meeeee, M. M.; Meeee, M. M.; Meeeeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
[123] | Meeeee, M. M.; Meeeeeee, M. M., MM 888 888, (8888); Meee. Meeee., (8888) 888, 88888. |
[124] | Meeeeeee, M.; Meeeeüeeee, M.; Meeeeeüeeee, M., Meeeeee. Meee., (8888) 888, 888. |
[125] | Meeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
[126] | Meeeeee, M.; Meüeeee, M., MM 8 888 888, (8888); Meee. Meeee., (8888) 88, 888888. |
[127] | Meeeee, M. M.; Mee, M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 88.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.