DOI: 10.1021/jo971010u. A Reexamination of the Mechanism of the Biginelli Dihydropyrimidine Synthesis. Support for an <i>N</i>-Acyliminium Ion Intermediate<sup>1</sup>

A Reexamination of the Mechanism of the Biginelli Dihydropyrimidine Synthesis. Support for an N-Acyliminium Ion Intermediate1

10.1021/jo971010u

Crossref journal-article

American Chemical Society (ACS)

The Journal of Organic Chemistry (316)

Bibliography

Kappe, C. O. (1997). A Reexamination of the Mechanism of the Biginelli Dihydropyrimidine Synthesis. Support for an N-Acyliminium Ion Intermediate1. The Journal of Organic Chemistry, 62(21), 7201â7204.

Authors 1

C. Oliver Kappe (first)

References 25 Referenced 401

{'volume-title': 'O. P.', 'year': '1997', 'author': 'Synthesis', 'key': 'jo971010ub00001/jo971010ub00001_1'} / O. P. by Synthesis (1997)
{'key': 'jo971010ub00002/jo971010ub00002_1', 'first-page': '416', 'volume': '23', 'author': 'Biginelli P.', 'year': '1893', 'journal-title': 'Gazz. Chim. Ital.'} / Gazz. Chim. Ital. by Biginelli P. (1893)
{'key': 'jo971010ub00003/jo971010ub00003_1', 'first-page': '6963', 'volume': '49', 'author': 'For', 'year': '1993', 'journal-title': 'Tetrahedron'} / Tetrahedron by For (1993)
{'key': 'jo971010ub00004/jo971010ub00004_1', 'first-page': '2797', 'volume': '62', 'author': 'Kappe C. O.', 'year': '1997', 'journal-title': 'J. Org. Chem.'} / J. Org. Chem. by Kappe C. O. (1997)
{'key': 'jo971010ub00005/jo971010ub00005_1', 'first-page': '1188', 'volume': '26', 'author': "O'Reilly B. C.", 'year': '1987', 'journal-title': 'Heterocycles'} / Heterocycles by O'Reilly B. C. (1987)
{'key': 'jo971010ub00006/jo971010ub00006_1', 'first-page': '7822', 'volume': '36', 'author': 'Wipf P.', 'year': '1995', 'journal-title': 'Tetrahedron Lett.'} / Tetrahedron Lett. by Wipf P. (1995)
10.1002/anie.199115591 / Angew. Chem., Int. Ed. Engl. by Goldman S. (1991)
10.1021/jm00106a048 / J. Med. Chem. by Atwal K. S. (1991)
{'key': 'jo971010ub00009/jo971010ub00009_1', 'volume': '58', 'author': 'Snider B. B.', 'year': '1993', 'journal-title': 'J. Org. Chem.'} / J. Org. Chem. by Snider B. B. (1993)
10.1021/jo00110a021 / J. Org. Chem. by Patil A. D. (1995)
10.1021/ja00206a029 / J. Am. Chem. Soc. by Kashman Y. (1989)
{'key': 'jo971010ub00012/jo971010ub00012_1', 'first-page': '3237', 'volume': '58', 'author': 'Overman L. E.', 'year': '1993', 'journal-title': 'J. Org. Chem.'} / J. Org. Chem. by Overman L. E. (1993)
{'key': 'jo971010ub00013/jo971010ub00013_1', 'first-page': '3791', 'volume': '55', 'author': 'Folkers K.', 'year': '1933', 'journal-title': 'J. Am. Chem. Soc.'} / J. Am. Chem. Soc. by Folkers K. (1933)
10.1021/ja00807a040 / J. Am. Chem. Soc. by Sweet F. (1973)
10.1021/ja01348a041 / J. Am. Chem. Soc. by Folkers K. (1932)
10.1021/ja01334a044 / J. Am. Chem. Soc. by Folkers K. (1933)
Heathcock, C. H.Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford; 1991; Vol. 2, p 133−179. Nielson, A. T.; Houlihan, W.Org. React. (N.Y.)1968,16, 1−438. (10.1016/B978-0-08-052349-1.00027-5)
10.1002/jhet.5570260112 / J. Heterocycl. Chem. by Kappe C. O. (1989)
{'key': 'jo971010ub00020/jo971010ub00020_1', 'first-page': '1192', 'volume': '26', 'author': 'For', 'year': '1987', 'journal-title': 'Heterocycles'} / Heterocycles by For (1987)
Donleavy, J. J.; Kise, M. A.Org. Synth.1943,Collect. Vol. II, 422−423.
10.1248/cpb.6.479 / Chem. Pharm. Bull. by Senda S. (1958)
{'key': 'jo971010ub00023/jo971010ub00023_1', 'first-page': '213', 'volume': '151', 'author': 'Schiff H.', 'year': '1869', 'journal-title': 'Ann.'} / Ann. by Schiff H. (1869)
{'key': 'jo971010ub00024/jo971010ub00024_1', 'first-page': '377', 'volume': '291', 'author': 'Schiff H.', 'year': '1896', 'journal-title': 'Ann.'} / Ann. by Schiff H. (1896)
Overman, L. E.; Ricca, D. J.Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford; Vol. 2, 1991; p 1007−1046. Hiemstra, H.; Speckamp, W. N.Comprehensive OrganicSynthesis; Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford; Vol. 2, 1991; p 1047−1082, and references therein.
{'key': 'jo971010ub00026/jo971010ub00026_1', 'first-page': '379', 'volume-title': '11th IUPAC Conference on Organic Synthesis', 'author': 'Okamoto K. T.', 'year': '1984'} / 11th IUPAC Conference on Organic Synthesis by Okamoto K. T. (1984)

Dates

Type	When
Created	23 years, 1 month ago (July 26, 2002, 1:11 a.m.)
Deposited	3 years, 10 months ago (Oct. 17, 2021, 2:10 a.m.)
Indexed	1 day, 22 hours ago (Sept. 4, 2025, 9:57 a.m.)
Issued	27 years, 11 months ago (Oct. 1, 1997)
Published	27 years, 11 months ago (Oct. 1, 1997)
Published Online	27 years, 10 months ago (Oct. 17, 1997)
Published Print	27 years, 11 months ago (Oct. 1, 1997)

Funders 0

None

BibTeX

@article{Kappe_1997, title={A Reexamination of the Mechanism of the Biginelli Dihydropyrimidine Synthesis. Support for an N-Acyliminium Ion Intermediate1}, volume={62}, ISSN={1520-6904}, url={http://dx.doi.org/10.1021/jo971010u}, DOI={10.1021/jo971010u}, number={21}, journal={The Journal of Organic Chemistry}, publisher={American Chemical Society (ACS)}, author={Kappe, C. Oliver}, year={1997}, month=oct, pages={7201–7204} }

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