APPLICATION OF SULFONIC ACID FUNCTIONALIZED NANOPOROUS SILICA
                  (SBA-Pr-SO<sub>3</sub>H) FOR THE PREPARATION OF
                  4,6-DIARYLPYRIMIDIN-2(1<i>H</i>)-ONES

Ziarani, Ghodsi Mohammadi; Azizi, Masoumeh; Hajiabbasi, Parvin; Badiei, Alireza

doi:10.5935/0100-4042.20150033

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Artigo • Quím. Nova 38 (4) • May 2015 • https://doi.org/10.5935/0100-4042.20150033 copy

APPLICATION OF SULFONIC ACID FUNCTIONALIZED NANOPOROUS SILICA (SBA-Pr-SO₃H) FOR THE PREPARATION OF 4,6-DIARYLPYRIMIDIN-2(1H)-ONES

Authorship SCIMAGO INSTITUTIONS RANKINGS

In this work, we report the Biginelli-type reaction between various aldehydes, acetophenones and urea systems in the presence of sulfonic acid functionalized silica (SBA-Pr-SO₃H) under solvent-free conditions, which led to 4,6-diarylpyrimidin-2(1H)-ones derivatives. SBA-Pr-SO₃H with a pore size of 6 nm was found to be an efficient heterogeneous solid acid catalyst for this reaction which led to high product yields, was environmentally benign with short reaction times and easy handling.

Biginelli-type reaction; green synthesis; heterogeneous SBA-Pr-SO₃H catalyst

Entry	R₁	R₂	Product	Time (min)	Yield (%)	mp (°C)	mp (Lit)
1	H	H	4a	20	96	231-234	227-228 [45]
2	4-Cl	H	4b	25	93	260-262	258-260 [32]
3	4-Me	H	4c	35	97	288-291	287-290 [32]
4	3-Me	H	4d	40	97	275-278	-
5	4-OH	H	4e	20	91	258-260	264-265 [45]
6	4-OMe	H	4f	30	97	257-260	244-245 [45]
7	H	4-Me	4g	30	92	285-289	-
8	4-Cl	4-NO₂	4h	30	94	309-311	308-310 [32]
9	4-Cl	4-OMe	4i	30	93	310-312	312-314 [32]

Entry	Temperature (°C)	Time (h)	Yield (%)
1	rt.	5	Trace
2	50	5	30
3	70	20 min	65
5	110	20 min	96
6	140	20 min	96

Entry	Catalyst	Condition	Time (min)	Yield (%)	Year	Ref.
1	I₂	neat/ 140°C	1.20-2.15 h	60-96	2009	[33]
2	H₂NSO₃H	neat/ 70°C	15-60	91-99	2008	[32]
3	Bi(TFA)₃	neat/ 70°C	30-85	60-95	2007	[31]
4	SBA-Pr-SO₃H	neat/ 110°C	20-40	91-97	This work

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APPLICATION OF SULFONIC ACID FUNCTIONALIZED NANOPOROUS SILICA (SBA-Pr-SO3H) FOR THE PREPARATION OF 4,6-DIARYLPYRIMIDIN-2(1H)-ONES

APPLICATION OF SULFONIC ACID FUNCTIONALIZED NANOPOROUS SILICA (SBA-Pr-SO₃H) FOR THE PREPARATION OF 4,6-DIARYLPYRIMIDIN-2(1H)-ONES