An Efficient Protocol for Facile Synthesis of New 5-Substituted-1<i>H</i>-Tetrazole Derivatives Using Copper-Doped Silica Cuprous Sulfate (CDSCS) as Heterogeneous Nano-Catalyst

Rad, Mohammad Navid Soltani

doi:10.5935/0103-5053.20160138

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Journal of the Brazilian Chemical Society

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Articles • J. Braz. Chem. Soc. 28 (1) • Jan 2017 • https://doi.org/10.5935/0103-5053.20160138 copy

An Efficient Protocol for Facile Synthesis of New 5-Substituted-1H-Tetrazole Derivatives Using Copper-Doped Silica Cuprous Sulfate (CDSCS) as Heterogeneous Nano-Catalyst

Authorship SCIMAGO INSTITUTIONS RANKINGS

A facile and highly efficient protocol for synthesis of new 5-substituted-1H-tetrazoles derivatives using copper-doped silica cuprous sulfate (CDSCS) is described. In this method, the cycloaddition reaction of sodium azide with structurally diverse nitriles involving bioactive N-heterocyclic cores exploiting CDSCS in refluxing H₂O/i-PrOH (1:1, v/v) furnishes the corresponding 5-substituted-1H-tetrazoles in good to excellent yields (up to 93%). The influence of parameters effective in progress of reaction including solvent type, temperature and catalyst was studied and discussed. In this protocol, CDSCS was proved to be an efficient heterogeneous nano-catalyst to easily achieve the new tetrazole derivatives. The advantages of CDSCS in current protocol known are its cheapness, thermal and chemical stability, ease of recyclability and reusability for several consecutive runs without significant decline in its reactivity.

Keywords:
azide; CDSCS; cycloaddition; nitrile; 1H-tetrazole


	Solvent	T / ºC	time / h	Yield^b b isolated yield; / %
1	H₂O	r.t.	24	19
2	H₂O	50	10	28
3	H₂O	60	7	39
4	H₂O	70	7	42
5	H₂O	80	5	50
6	H₂O	reflux	4	58
7	H₂O/i-PrOH^c c 1:1 (v/v).	r.t.	18	62
8	H₂O/i-PrOH^c c 1:1 (v/v).	reflux	4	93
9	H₂O/Me₂CO^c c 1:1 (v/v).	reflux	6	40
10	H₂O/DMF^c c 1:1 (v/v).	reflux	7	46
11	H₂O/DMSO^c c 1:1 (v/v).	reflux	7	49
12	H₂O/NMP^c c 1:1 (v/v).	reflux	6	53
13	H₂O/HMPA^c c 1:1 (v/v).	reflux	7	50
14	H₂O/THF^c c 1:1 (v/v).	reflux	8	81
15	THF	reflux	12	46
16	i-PrOH	reflux	5	60


entry	Catalyst	time / h	Yield^b b isolated yield; / %
1	TBAF^c c an equimolar amount was used;	24	40
2	NH₄Cl^c c an equimolar amount was used;	24	59
3	Et₃N.HCl^c c an equimolar amount was used;	12	75
4	FeCl₃–SiO₂^c c an equimolar amount was used;	24	54
5	CDSCS^d d 0.05 mol%;	4	93
6	amberlyst-15^c c an equimolar amount was used;	24	30
7	HCl^c c an equimolar amount was used;	24	48
8	silica sulfuric acid^c c an equimolar amount was used;	12	79
9	Cu₂O^c c an equimolar amount was used;	10	67
10	CuFe₂O₄^c c an equimolar amount was used;	12	70
11	Zeolite^d d 0.05 mol%;	24	52
12	ZnBr₂^c c an equimolar amount was used;	5	67
13	ZnO^c c an equimolar amount was used;	15	53
14	AlCl₃^c c an equimolar amount was used;	10	72
15	TMSCl^c c an equimolar amount was used;	12	41
16	H₃PW₁₂O₄₀^e e 1 mol%.	8	50

entry	time / h	Yield^c c isolated yield. / %
1	4	93
2	4	89
3	5	85
4	6	87
5	3.5	83
6	5.5	82
7	3	87
8	3.5	91
9	4	90
10	7	86
11	4	89
12	5.5	92
13	6	91
14	6	89
15	6	90


entry^b b the entry number corresponds to the trial number;	time / h	Yield^c c isolated yield. / %
1	4	93
2	4	93
3	4.5	91
4	4.5	90
5	5	87

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entry	time / h	Yield^c c isolated yield. / %
1	4	93
2	4	89
3	5	85
4	6	87
5	3.5	83
6	5.5	82
7	3	87
8	3.5	91
9	4	90
10	7	86
11	4	89
12	5.5	92
13	6	91
14	6	89
15	6	90

entry	time / h	Yield^c c isolated yield. / %
1	4	93
2	4	89
3	5	85
4	6	87
5	3.5	83
6	5.5	82
7	3	87
8	3.5	91
9	4	90
10	7	86
11	4	89
12	5.5	92
13	6	91
14	6	89
15	6	90

entry	time / h	Yield^c c isolated yield. / %
1	4	93
2	4	89
3	5	85
4	6	87
5	3.5	83
6	5.5	82
7	3	87
8	3.5	91
9	4	90
10	7	86
11	4	89
12	5.5	92
13	6	91
14	6	89
15	6	90