1
10
M. M. Heravi et al.: Deamination of Some N-Amino Nitrogen Heterocycles
Catalyst Preparation
Preyssler’s anion, H [NaP W O110], was prepared by pas-
sage of a solution of the potassium salt in water through
a column (50 cmꢂ1 cm) of Dowex50 Wꢂ8 in the Hþ form
and evaporation of the elute to dryness under vacuum [18].
van Koningsbruggen PJ, van Hal JW, de GraaV RAG,
Haasnoot JG, Reedijik J (1993) J Chem Soc Dalton
Trans 2163; e) Liu JC, Fu DG, Zhuang JZ, Duan CY,
You XZ (1999) J Chem Soc Dalton Trans 2337
1
4
5
30
[
5] a) Schmidt RR, Heermann D (1981) Chem Ber 114:
2
825; b) Khare GP, Sidwell RW, Witkowski JT, Simon
LN, Robins RK (1973) Antimikrob Ag Chemother 3:
17
Deamination of Amino Heterocycles: General Procedure
A mixture of 10 mmol heterocyclic N-amines 1–7, pre-
5
[
[
[
6] Hanna NB, Dimitrijevich SD, Larson SB, Robins RK,
Revankar GR (1988) J Heterocycl Chem 25: 1857
7] Witkowski JT, Robins RK, Sidwell RW, Simon LN
pared according to Ref. [22], and 0.74mg Preyssler’s anion
(
3
0.1mmol) was refluxed in 10 cm acetic acid for 24h. After
completion of the reaction (monitored by TLC) the mixture
was cooled to room temperature and the precipitated products
were separated by filtration, washed with cold ethanol, and
recrystallized from ethanol. The catalyst could be recycled
after evaporation of solvent from the residue solution and
washing with dichloroethane, and re-used in another reaction.
All products gave satisfactory spectral data in accord with the
assigned structures (Table 1).
(1972) J Med Chem 15: 1150
8] a) Camarasa M-J, De Las Heras FG (1983) J Heterocycl
Chem 20: 1307; b) De Las Heras FG, Camarasa M-J,
Martinez-Fern a´ ndez AR, Escario J-A (1984) Eur J Med
Chem – Chim Ther 19: 89
[9] Kozhevnikov IV (1987) Russ Chem Rev 56: 811
[
10] Izumi Y, Urabe K, Onaka K (1992) Zeolits Clay and
Heteropoly Acid in Organic Reaction, Vol. 99. Kodansha,
Tokyo
Acknowledgements
[11] OKuhara T, Mizuno N, Misono M (1996) Adv Catal 41:
13
12] Yadav GD, Bhagat RD (2005) J Mol Catal A: Chem 98:
35
13] Imamura K, Tano K, Kobeppn S (1998) Jpn Kokai
Tokkyo Koho JP Patent 1087811
14] Bamoharram FF, Heravi MM, Roshani M, Jahangir M,
Gharib A (2006) Appl Catal 42: 302
[15] Bamoharram FF, Heravi MM, Roshani M, Tavakoli N
(2006) J Mol Catal 252: 219
[16] Alizadeh MH, Razavi H, Bamoharram FF, Hassanzadeh
MH (2003) Kinet Catal 44: 524
[17] Bamoharram FF, Heravi MM, Roshani M, Jahangir M
(2006) J Mol Catal 252: 90
[18] Bamoharram FF, Heravi MM, Roshani M, Akbarpour M
(2006) J Mol Catal 255: 193
[19] Heravi MM, Behbahani FK, Bamoharram FF (2006) J
Mol Catal 253:16
1
The authors are thankful from Azzahra Research Council for
the partial financial support.
[
[
[
2
References
[
1] a) Coon M, Ball A, Pound J, Ap S, Hollenback D, White
T, Tulinsk J, Bonham L, Morrison DK, Finney R, Singer
JW (2003) Mol Cancer Ther 2: 1067; b) Moon HS,
Jacobson EM, Khersonsky SM, Luzung MR, Walsh
DP, Xiong W, Lee JW, Parikh PB, Lam JC, Kang
T-W, Rosania GR, Schier AF, Chang Y-T (2002) J
Am Chem Soc 124: 11608; c) Baindur N, Chadha N,
Brandt BM, Asgari D, Patch RJ, Schalk-HiHi C, Carver
TE, Petrounia IP, Baumann CA, Ott H, Springer BA,
Player MR (2005) J Med Chem 48: 1717; d) Whitten
JP, Xie YF, Erickson PE, Webb TR, De Souza EB,
Grigoriadis DE, McCarthy JR (2002) J Med Chem 39:
[20] Cheng J-P, Xian M, Wang K, Zhu X, Yin Z, Wang PG
(1998) J Am Chem Soc 120: 10266
4354; e) Tanabe A, Kawata K (2004) Anal Sci 20: 227
2] Xu LZ, Jiao K, Zhang SS, Kuang SP (2002) Bull Korean
Chem Soc 23: 1699
3] van Diemen JH, Haasnoot JG, Hage R, Reedijk J, Vos
JG, Wang RJ (1991) Inorg Chem 30: 4038
4] a) Slangen PM, van Koningsbruggen PJ, Goubitz K,
Haasnoot JG, Reedijk J (1994) Inorg Chem 33: 1121; b)
van Koningsbruggen PJ, Haasnoot JG, Kooijman H,
Reedijk J, Spek AL (1997) Inorg Chem 36: 2487; c)
Garcia Y, van Koningsbruggen PJ, Bravic G, Guionneau
P, Chasseau D, Cascarano GL, Moscovici J, Lambert K,
Michalowicz A, Kahn O (1997) Inorg Chem 36: 6357; d)
[
[
[
[21] Sousa AKMH, Sousa JR, Santiago MO, Longhinotti
E, Batista AA, Ellena J, Castellano EE, Lopes LGF,
Moreira IS (2005) Tetrahedron Lett 46: 1889
[22] a) Sharfi T, Heravi MM, Ghassemzadeh M, Neumuller
B (2005) ZAAC 112: 2297; b) Ghassemzadeh M,
Tabatabaee M, Pouramin MM, Heravi MM, Eslami A,
Neumuller B (2006) ZAAC 632: 786
[23] a) Heravi MM (1992) Iran J Chem Chem Eng 8: 11; b)
Heravi MM, Sadeghi MM, Froomand MF, Khaleghi S,
Ghassemzadeh M (2006) Indian J Het Chem 15(4): 411
and references cited therein