Silica-Supported Polyphosphoric Acid in the Synthesis of 4-Substituted Tetrahydroisoquinoline Derivatives
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental
3.1. General
3.2. Preparation of PPA/SiO2 Catalyst General Procedure
3.3. Typical Procedure for the Synthesis of 2-Amino-1,1-diphenylethanes 3
3.4. 2,2-Diphenylethanamine (3a): Known Compound [53]
3.5. Acylation of Amines 3: Typical Procedure for the Synthesis of Amides 4 and 6
3.6. Cyclization of Amides 4 and 6 in Acetic/Trifluoracetic Acid Milieu: Typical Procedure
3.7. Cyclization of Amides 4 and 6 in SiO2-Supported Milieu: Typical Procedure
4. Conclusions
Acknowledgments
References
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Sample Availability: Samples of the compounds are available from the authors. |
3 | R1 | Yield, % | M.p., °C | |
---|---|---|---|---|
a | H | H | 42 | 47–49 |
b | OCH3 | OCH3 | 82 | oil |
4 | R | R1 | R2 | Yield, % | M.p., °C |
---|---|---|---|---|---|
a | H | H | COCH3 | 80 | 85–86 |
b | H | H | SO2CH3 | 98 | 138–139 |
c | H | H | COPhPh | 94 | 192–193 |
d | OCH3 | OCH3 | COCH3 | 91 | 126–128 |
e | OCH3 | OCH3 | SO2CH3 | 90 | 49–52 |
f | OCH3 | OCH3 | COPhPh | 97 | 200–202 |
5 | R | R1 | R2 | Yield, % (CH3COOH:CF3COOH = 4:1) | Yield, % (SiO2/PPA) |
---|---|---|---|---|---|
a | H | H | COCH3 | 90 | 94 |
b | H | H | SO2CH3 | 80 | 91 |
c | H | H | COPhPh | 84 | 96 |
d | OCH3 | OCH3 | COCH3 | 85 | 96 |
e | OCH3 | OCH3 | SO2CH3 | 87 | 97 |
f | OCH3 | OCH3 | COPhPh | 87 | 98 |
6 | R2 | Yield, % | M.p., °C |
a | COCH3 | 98 | Oil |
b | SO2CH3 | 98 | Oil |
c | COPhPh | 98 | 156–157 |
7 | R2 | Yield, % | m.p., °C |
a | COCH3 | 89 | Oil |
b | SO2CH3 | 93 | 66–67 |
c | COPhPh | 96 | Oil |
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Manolov, S.; Nikolova, S.; Ivanov, I. Silica-Supported Polyphosphoric Acid in the Synthesis of 4-Substituted Tetrahydroisoquinoline Derivatives. Molecules 2013, 18, 1869-1880. https://doi.org/10.3390/molecules18021869
Manolov S, Nikolova S, Ivanov I. Silica-Supported Polyphosphoric Acid in the Synthesis of 4-Substituted Tetrahydroisoquinoline Derivatives. Molecules. 2013; 18(2):1869-1880. https://doi.org/10.3390/molecules18021869
Chicago/Turabian StyleManolov, Stanimir, Stoyanka Nikolova, and Iliyan Ivanov. 2013. "Silica-Supported Polyphosphoric Acid in the Synthesis of 4-Substituted Tetrahydroisoquinoline Derivatives" Molecules 18, no. 2: 1869-1880. https://doi.org/10.3390/molecules18021869