A Catalyst-Free, Temperature-Driven One-Pot Synthesis of 1-Adamantylhydrazine Hydrochloride

Anjana Delpe Acharige; Raul Neri; James Hodgson; Stefan H. Bossmann

doi:10.1055/s-0040-1707353

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(22): 3374-3377
DOI: 10.1055/s-0040-1707353

psp

A Catalyst-Free, Temperature-Driven One-Pot Synthesis of 1-Adamantylhydrazine Hydrochloride

Anjana Delpe Acharige

,

Raul Neri

,

James Hodgson

,

Stefan H. Bossmann ∗

Department of Chemistry, Kansas State University, CBC Building 201, Manhattan, KS, 66506-0401, USA eMail: sbossman@ksu.edu

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

1-Adamantylhydrazine can be a versatile intermediate for many biologically active compounds as adamantyl possesses a wide spectrum of medicinal properties. Described here is a detailed one-pot synthesis of 1-adamantylhydrazine, carried out on a milligram to gram scale, that steadily delivers a highly stable product used to carry out the synthesis of 1-(adamantan-1-yl)-1H-pyrazol-3-amine for bacterial studies. The reaction employs inexpensive, catalyst free, readily available starting materials. In the synthesis of 1-(adamantan-1-yl)-1H-pyrazol-3-amine, the use of a continuous extraction method allows for complete extraction of the target product into the organic layer and increases the overall percentage yield.

Key words

S_N1 substitution - hydrazines - adamantane - 1H-pyrazol-3-amine - continuous extraction

Volltext

Referenzen

References
1 Fort RC. Adamantane: The Chemistry of Diamond Molecules. In Studies in Organic Chemistry, Vol. 5. Marcel Dekker; New York: 1976
2 Stella V, Borchardt R, Hageman M, Oliyai R, Maag H, Tilley J. Prodrugs: Challenges and Rewards, Part 1. Springer; New York: 2007
3 Davies WL, Grunert RR, Haff RF, McGahen JW, Neumayer EM, Paulshock M, Watts JC, Wood TR, Hermann EC, Hoffmann CE. Science 1964; 144: 862
4 Khaziev R, Shtyrlin N, Pavelyev R, Nigmatullin R, Gabbasova R, Grishaev D, Shtro A, Galochkina A, Nikolaeva Y, Vinogradova T, Manicheva O, Dogonadze M, Gnezdilov O, Sokolovich E, Yablonskiy P, Balakin K, Shtyrlin Y. Lett. Drug Des. Discov. 2019; 1360
5 Kukushkin ME, Skvortsov DA, Kalinina MA, Tafeenko VA, Burmistrov VV, Butov GM, Zyk NV, Majouga AG, Beloglazkina EK. Beilstein Arch. 2019; 2019143
6 Augeri DJ, Robl JA, Betebenner DA, Magnin DR, Khanna A, Robertson JG, Wang A, Simpkins LM, Taunk P, Huang Q, Han S.-P, Abboa-Offei B, Cap M, Xin L, Tao L, Tozzo E, Welzel GE, Egan DM, Marcinkeviciene J, Chang SY, Biller SA, Kirby MS, Parker RA, Hamann LG. J. Med. Chem. 2005; 48: 5025
7 Lamoureux G, Artavia G. Curr. Med. Chem. 2010; 17: 2967
8 Shvekhgeimer M.-GA. Russ. Chem. Rev. 1996; 65: 555
9 Li Q, Jin C, Petukhov PA, Rukavishnikov AV, Zaikova TO, Phadke A, LaMunyon DH, Lee MD, Keana JF. W. J. Org. Chem. 2004; 69: 1010
10 Olah GA, Surya Prakash GK, Shih JG, Krishnamurthy VV, Mateescu GD, Liang G, Sipos G, Buss V, Gund TM, Ragué Schleyer PV. J. Am. Chem. Soc. 1985; 107: 2764
11 Sunko D, Hiršl-Starčević S, Pollack S, Hehre W. J. Am. Chem. Soc. 1979; 101: 6163
12 Haeili M, Moore C, Davis CJ. C, Cochran JB, Shah S, Shrestha TB, Zhang Y, Bossmann SH, Benjamin WH, Kutsch O, Wolschendorf F. Antimicrob. Agents Chemother. 2014; 58: 3727
13 Wolschendorf F, Ackart D, Shrestha TB, Hascall-Dove L, Nolan S, Lamichhane G, Wang Y, Bossmann SH, Basaraba RJ, Niederweis M. Proc. Natl. Acad. Sci. U. S. A. 2011; 108: 1621
14 Dalecki AG, Malalasekera AP, Schaaf K, Kutsch O, Bossmann SH, Wolschendorf F. Metallomics 2016; 8: 412
15 Wanka L, Iqbal K, Schreiner PR. Chem. Rev. 2013; 113: 3516
16 Ohno M, Ishizaki K, Eguchi S. J. Org. Chem. 1988; 53: 1285
17 Daeniker HU. Helv. Chim. Acta 1967; 50: 2008
18 Butov GM, Mokhov VM. Russ. J. Org. Chem. 2018; 54: 1760
19 Thomas T, Shetty B. (Pennwalt Corporation, Philadelphia, PA, USA) US3719710A, 1973
20 Ji N, Meredith E, Liu D, Adams CM, Artman GD, Jendza KC, Ma F, Mainolfi N, Powers JJ, Zhang C. Tetrahedron Lett. 2010; 51: 6799

Zusatzmaterial

Supporting Information