Abstract
Hydrazine hydrate with acetic and propionic acids was an efficient reagent for acylation of primary and secondary amines at reflux temperatures. The reported one-pot method is high-yielding, simple, mild, and inexpensive.
ACKNOWLEDGMENTS
The authors thank Karnatak University, Dharwad, and University Grants Commission, New Delhi, India, for financial support and thankful to the University Sophisticated Instruments Centre, Karnatak University, Dharwad, for providing the spectral data.
Notes
a
All the products were identified by comparison of their 1H NMR, IR, mp, and bp with literature reports.[
Citation
19
]
b
Based on recovery of the starting material, no acetylation was observed even after 24 h.
a
All the products were identified by comparison of their 1H NMR, IR, mp, and bp with literature reports.[
Citation
19
]
b
Based on recovery of the starting material, no propionylation was observed even after 24 h.
(a)
Furniss
,
B. S.
;
Hannaford
,
A. J.
;
Smith
,
P. W. G.
;
Tatchell
,
A. R.
Vogel's Textbook of Practical Organic Chemistry, 5th ed.
;
Addison Wesley Longman
: Harlow ,
England (UK)
,
1997
; pp.
1348
–
1379
;
(b) Paul, S.; Nanda, P.; Gupta, R.; Loupy, A. Ac2O–Py/basic alumina as a versatile reagent for acetylations in solvent-free conditions under microwave irradiation. Tetrahedron Lett. 2002, 43, 4261–4265; (c) Shaffer, C. L.; Harriman, S.; Koen, Y. M; Hanzlik, R. P. Formation of Cyclopropanone during Cytochrome P450-Catalyzed N-Dealkylation of a Cyclopropylamine. J. Am. Chem. Soc. 2002, 124, 8268–8274; (d) Hwang, Y. C.; Chu, M.; Fowler, F. W. A synthesis of alpha-substituted amines. J. Org. Chem. 1985, 50, 3885–3890; (e) Hama, T.; Culkin, D. A.; Hartwig, J. F. Palladium-catalyzed intermolecular α-arylation of zinc amide enolates under mild conditions. J. Am. Chem. Soc. 2006, 128, 4976– 4985
.
(a)
Furniss
,
B. S.
;
Hannaford
,
A. J.
;
Smith
,
P. W. G.
;
Tatchell
,
A. R.
Vogel's Textbook of Practical Organic Chemistry, 5th ed.
;
Addison Wesley Longman
: Harlow ,
England (UK)
,
1997
; pp.
1348
–
1379
;
(b) Paul, S.; Nanda, P.; Gupta, R.; Loupy, A. Ac2O–Py/basic alumina as a versatile reagent for acetylations in solvent-free conditions under microwave irradiation. Tetrahedron Lett. 2002, 43, 4261–4265; (c) Shaffer, C. L.; Harriman, S.; Koen, Y. M; Hanzlik, R. P. Formation of Cyclopropanone during Cytochrome P450-Catalyzed N-Dealkylation of a Cyclopropylamine. J. Am. Chem. Soc. 2002, 124, 8268–8274; (d) Hwang, Y. C.; Chu, M.; Fowler, F. W. A synthesis of alpha-substituted amines. J. Org. Chem. 1985, 50, 3885–3890; (e) Hama, T.; Culkin, D. A.; Hartwig, J. F. Palladium-catalyzed intermolecular α-arylation of zinc amide enolates under mild conditions. J. Am. Chem. Soc. 2006, 128, 4976– 4985
.