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Автор: Grafiati
Опубліковано: 4 червня 2021
Оновлено: 21 лютого 2023

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1

Moser, Shasta, Ryan Church, M. Brad Peori, and Keith Vaughan. "Triazene derivatives of (1,x)-diazacycloalkanes. Part IV.1 Synthesis and characterization of 1-[2-aryl-1-diazenyl]-3-(3-[2-aryl-1-diazenyl]hexahydro-1-pyrimidinylmethyl)hexahydropyrimidines and 1-(5,5-dimethyl-3-[2-aryl-1-diazenyl]hexahydro-1-pyrimidinylmethyl)-5,5-dimethyl-3-[2-aryl-1-diazenyl]hexahydropyrimidines from the reaction of diazonium salts with mixtures of formaldehyde and 1,3-diaminopropanes." Canadian Journal of Chemistry 83, no. 8 (August 1, 2005): 1071–83. http://dx.doi.org/10.1139/v05-131.

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Анотація:
Two new series of bistriazenes have been synthesized from a general reaction of diazonium salts with a mixture of a propanediamine and formaldehyde. Such reaction with 1,3-diaminopropane itself affords the 1-[2-aryl-1-diazenyl]-3-(3-[2-aryl-1-diazenyl]hexahydro-1-pyrimidinylmethyl)hexahydropyrimidines (6). 2,2-Dimethyl-1,3-diamino propane reacts in an analogous manner to give the 1-(5,5-dimethyl-3-[2-aryl-1-diazenyl]hexahydro-1-pyrimidinylmethyl)- 5,5-dimethyl-3-[2-aryl-1-diazenyl]hexahydropyrimidines (7). All new compounds have been characterized by IR and NMR spectroscopy, with elemental analysis or high resolution mass spectrometry of most of the new compounds. NMR assignments have been analyzed by a series of DEPT, COSY, and HSQC experiments. One example of each series has been unequivocally characterized by X-ray crystallography. The general conclusion of this study is that alkanediamines with three carbon atoms in the spacer link between the nitrogen atoms give rise to the linear bicyclic molecules of type 18, in contrast to the case of ethylenediamine (spacer link has two carbon atoms), which affords cage-like molecules of type 17.Key words: bistriazene, hexahydropyrimidine, diazonium coupling, formaldehyde, diaminopropane, nuclear magnetic resonance.
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2

Badamshin, A. G., D. R. Latypova, and V. A. Dokichev. "Synthesis of Polyfunctionalized Hexahydropyrimidines." Russian Journal of Organic Chemistry 55, no. 2 (February 2019): 168–73. http://dx.doi.org/10.1134/s1070428019020076.

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3

Zelenin, Kirill N., Valeriy V. Alekseyev, Ilya V. Ukraintsev, and Igor V. Tselinsky. "2-SUBSTITUTED HEXAHYDROPYRIMIDINES AND THEIR TAUTOMERISM." Organic Preparations and Procedures International 30, no. 1 (February 1998): 53–61. http://dx.doi.org/10.1080/00304949809355259.

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4

Katritzky, Alan R., Sandeep K. Singh, and Hai-Ying He. "Novel Syntheses of Hexahydropyrimidines and Tetrahydroquinazolines." Journal of Organic Chemistry 67, no. 9 (May 2002): 3115–17. http://dx.doi.org/10.1021/jo010927x.

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5

Luk'yanov, O. A., G. V. Pokhvisneva, and T. V. Ternikova. "N,N?-Diacylated imidazolidines and hexahydropyrimidines." Russian Chemical Bulletin 43, no. 8 (August 1994): 1376–80. http://dx.doi.org/10.1007/bf00703698.

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6

Farrell, Joshua R., Jonathan Niconchuk, Christine S. Higham, and Brittany W. Bergeron. "Phenol derivatized hexahydropyrimidines prepared from Mannich condensations." Tetrahedron Letters 48, no. 45 (November 2007): 8034–36. http://dx.doi.org/10.1016/j.tetlet.2007.09.038.

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7

Shafikova, E. A., D. V. Petrov, T. A. Sapozhnikova, N. J. Baschenko, and V. A. Dokichev. "Synthesis of norbornane series tetra- and hexahydropyrimidines." Chemistry of Heterocyclic Compounds 45, no. 6 (June 2009): 685–90. http://dx.doi.org/10.1007/s10593-009-0328-1.

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8

Tingley, Reid, M. Brad Peori, Ryan Church, and Keith Vaughan. "Triazene derivatives of (1,x)-diazacycloalkanes. Part V.1 Synthesis and characterization of 4-ethyl-3-({6-ethyl-3-[2-aryl-1-diazenyl]hexahydro-1-pyrimidinyl}methyl)-1-[2-aryl-1-diazenyl)hexa- hydropyrimidines from the reaction of diazonium salts with mixtures of formaldehyde and 1,3-diaminopentane." Canadian Journal of Chemistry 83, no. 10 (October 1, 2005): 1799–807. http://dx.doi.org/10.1139/v05-192.

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Анотація:
A new series of bistriazenes has been synthesized from a general reaction of diazonium salts with a mixture of 1,3-diaminopentane (DYTEK® EP diamine) and formaldehyde, which affords the 4-ethyl-3-({6-ethyl-3-[2-aryl-1-diazenyl]hexahydro-1-pyrimidinyl}methyl)-1-[2-aryl-1-diazenyl]hexahydropyrimidines (1). Each of the molecules of type 1 is built up of two equivalent 3-(aryldiazenyl)-6-ethylhexahydro-1-pyrimidinyl groups attached to a central methylene group. The importance of this study is in part due to the fact that the formaldehyde–1,3-diaminopentane system has not previously been investigated. All new compounds have been characterized by IR and NMR spectroscopy, with elemental analysis for selected compounds; one example from the series has been unequivocally characterized by X-ray crystallography. Although analysis of the NMR spectra is made somewhat difficult because of broadness and coalescence of signals due to the rotational dynamics of the N—N single bonds, it is possible to fully assign the proton spectra of all compounds and to detect 94% of all carbon signals. The fine structure within the proton spectra illustrate the diastereotopic nature of the methylene group protons because of the presence of a stereocenter in each hexahydropyrimidine ring. The general conclusion of this study is that alkanediamines with three carbon atoms in the spacer link between the nitrogen atoms give rise to the linear bicyclic molecules of type 1, 2, and 3, in contrast to the case of ethylenediamine (spacer link has two carbon atoms), which affords molecules of type 7 that exemplify the bridged bicyclic bistriazene structure. The new compounds of series 1 represent an extension of a broad ranging study of the synthesis of new bistriazene derivatives of (1,x)-diazacycloalkanes.Key words: triazene, diazonium coupling, hexahydropyrimidine, diaminopentane, diazacycloalkanes, stereocenter, diastereotopic protons.
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9

Bergeron, Raymond J., and Howard W. Seligsohn. "Hexahydropyrimidines as masked spermidine vectors in drug delivery." Bioorganic Chemistry 14, no. 4 (December 1986): 345–55. http://dx.doi.org/10.1016/0045-2068(86)90001-5.

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10

LUK'YANOV, O. A., G. V. POKHVISNEVA, and T. V. TERNIKOVA. "ChemInform Abstract: N,N′-Diacylated Imidazolidines and Hexahydropyrimidines." ChemInform 26, no. 12 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199512067.

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11

ZELENIN, K. N., V. V. ALEKSEYEV, I. V. UKRAINTSEV, and I. V. TSELINSKY. "ChemInform Abstract: 2-Substituted Hexahydropyrimidines and Their Tautomerism." ChemInform 29, no. 24 (June 22, 2010): no. http://dx.doi.org/10.1002/chin.199824134.

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12

Katritzky, Alan R., Sandeep K. Singh, and Hai-Ying He. "ChemInform Abstract: Novel Syntheses of Hexahydropyrimidines and Tetrahydroquinazolines." ChemInform 33, no. 52 (May 18, 2010): no. http://dx.doi.org/10.1002/chin.200252148.

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13

Janati, Fatemeh, Majid M. Heravi, and Ahmad Mirshokraie. "Superparamagnetic Iron Oxide as an Efficient Catalyst for the One-Pot, Solvent-Free Synthesis of 5,5-Disubstituted Hexahydropyrimidines and Their Spiro Analogues." Journal of Chemistry 2013 (2013): 1–5. http://dx.doi.org/10.1155/2013/214617.

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Анотація:
Superparamagnetic Fe3O4is shown to act as a very efficient catalyst for the one-pot, three-component synthesis of 5,5-disubstituted hexahydropyrimidines and their spiropiperidines. The catalyst is easily recovered by the use of an external magnet and reused in several reactions without any noticeable loss of activity. The products are obtained in short time and good purity upon separation of the catalyst and evaporation of the volatiles of the reaction mixture.
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14

KNABE, J., and J. BIWERSI. "ChemInform Abstract: Racemates and Enantiomers of 5,5-Disubstituted Hexahydropyrimidines." ChemInform 25, no. 16 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199416191.

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15

Göblyös, Anikó, László Lázár, and Ferenc Fülöp. "Ring-chain tautomerism of 2-aryl-substituted-hexahydropyrimidines and tetrahydroquinazolines." Tetrahedron 58, no. 5 (January 2002): 1011–16. http://dx.doi.org/10.1016/s0040-4020(01)01196-6.

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16

Ahmed, Nayeem, Saima Tarannum, and Zeba N. Siddiqui. "Dy/chitosan: a highly efficient and recyclable heterogeneous nano catalyst for the synthesis of hexahydropyrimidines in aqueous media." RSC Advances 5, no. 63 (2015): 50691–700. http://dx.doi.org/10.1039/c5ra08160b.

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17

Tolpygin, I. E. "Chemosensor activity of 2-(anthracen-9-yl)-substituted imidazolidines and hexahydropyrimidines." Russian Journal of Organic Chemistry 48, no. 1 (January 2012): 104–8. http://dx.doi.org/10.1134/s1070428012010162.

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18

Garratt, Peter J., Simon N. Thorn, and Roger Wrigglesworth. "Regioselective and enantiospecific synthesis of 6-substituted and 5,6-disubstituted hexahydropyrimidines." Tetrahedron Letters 32, no. 5 (January 1991): 691–94. http://dx.doi.org/10.1016/s0040-4039(00)74861-1.

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19

Sosnovskikh, V. Ya, and V. A. Kutsenko. "Synthesis of 2-(2-hydroxyaroylmethylene)hexahydropyrimidines from 2-trichloromethylchromones and trimethylenediamine." Russian Chemical Bulletin 48, no. 11 (November 1999): 2117–20. http://dx.doi.org/10.1007/bf02494859.

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20

Korbonits, Dezsö, Erzsébet Tóbiás-Héja, and Pαl Kolonits. "Ring – Chain Tautomerism of 4-Hydroximino-hexahydropyrimidines Substituted in Position 2." Chemische Berichte 124, no. 5 (May 1991): 1199–202. http://dx.doi.org/10.1002/cber.19911240536.

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21

Zhou, Hui, Hetti Handi Chaminda Lakmal, Jonathan M. Baine, Henry U. Valle, Xue Xu, and Xin Cui. "Catalytic [2 + 2 + 2] cycloaddition with indium(iii)-activated formaldimines: a practical and selective access to hexahydropyrimidines and 1,3-diamines from alkenes." Chemical Science 8, no. 9 (2017): 6520–24. http://dx.doi.org/10.1039/c7sc02576a.

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22

Latypova, D. R. "Mannich-Type Reaction for Synthesis of Hexahydropyrimidines and 3,7-Diazabicyclo[3.3.1]Nonanes." Bashkir chemistry journal 25, no. 2 (August 2018): 10. http://dx.doi.org/10.17122/bcj-2018-2-10-23.

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23

Lorente, Antonio, José L. Garacia Navio, José C. Lopez Perez, and José L. Soto. "A Simple Synthesis of 4-Amino-6-aryl-2-thioxotetra-and -hexahydropyrimidines." Synthesis 1985, no. 01 (1985): 89–92. http://dx.doi.org/10.1055/s-1985-31121.

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24

Shakirov, R. R., T. V. Dokichev, R. Z. Biglova, N. M. Vlasova, N. Z. Baibulatova, and R. F. Talipov. "Methyl nitroacetate and 3-nitropropionate in the synthesis of hexahydropyrimidines and piperidines." Chemistry of Heterocyclic Compounds 44, no. 1 (January 2008): 43–49. http://dx.doi.org/10.1007/s10593-008-0011-y.

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25

Pokhvisneva, G. V., and O. A. Luk’yanov. "Synthesis of 2-substituted 1-tosyl-3-(1-tosyliminoalkyl)imidazolidines and-hexahydropyrimidines." Russian Chemical Bulletin 55, no. 5 (May 2006): 903–6. http://dx.doi.org/10.1007/s11172-006-0350-8.

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26

KALYANAM, N., P. C. PARTHASARATHY, L. ANANTHAN, S. G. MANJUNATHA, and M. A. LIKHATE. "ChemInform Abstract: Studies on Antiamoebic Compounds. Part 4. Synthesis of Hexahydropyrimidines and Tetrahydroimidazoles." ChemInform 23, no. 28 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199228071.

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27

Zohdi, Hussein F., Nora M. Rateb, and Sherif M. Elnagdy. "Green synthesis and antimicrobial evaluation of some new trifluoromethyl-substituted hexahydropyrimidines by grinding." European Journal of Medicinal Chemistry 46, no. 11 (November 2011): 5636–40. http://dx.doi.org/10.1016/j.ejmech.2011.09.036.

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28

Hwang, Jong Yeon, Hee-Young Kim, Suyeon Jo, Eunjung Park, Jihyun Choi, Sunju Kong, Dong-Sik Park, et al. "Synthesis and evaluation of hexahydropyrimidines and diamines as novel hepatitis C virus inhibitors." European Journal of Medicinal Chemistry 70 (December 2013): 315–25. http://dx.doi.org/10.1016/j.ejmech.2013.09.055.

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29

Sosnovskikh, V. Ya, and V. A. Kutsenko. "ChemInform Abstract: Synthesis of 2-(2-Hydroxyaroylmethylene)hexahydropyrimidines from 2-Trichloromethylchromones and Trimethylenediamine." ChemInform 31, no. 14 (June 9, 2010): no. http://dx.doi.org/10.1002/chin.200014136.

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30

GARRATT, P. J., S. N. THORN, and R. WRIGGLESWORTH. "ChemInform Abstract: Regioselective and Enantiospecific Synthesis of 6-Substituted and 5,6- Disubstituted Hexahydropyrimidines." ChemInform 22, no. 50 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199150159.

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31

Tolpygin, I. E. "ChemInform Abstract: Chemosensor Activity of 2-(Anthracen-9-yl)-Substituted Imidazolidines and Hexahydropyrimidines." ChemInform 43, no. 29 (June 21, 2012): no. http://dx.doi.org/10.1002/chin.201229176.

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32

KORBONITS, D., E. TOBIAS-HEJA, and P. KOLONITS. "ChemInform Abstract: Ring-Chain Tautomerism of 4-Hydroximino-hexahydropyrimidines Substituted in Position 2." ChemInform 22, no. 31 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199131084.

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33

KORBONITS, D., E. TOBIAS-HEJA, K. SIMON, and P. KOLONITS. "ChemInform Abstract: Solvent-Dependent Reversible Rearrangement of 4-(Hydroxyimino) hexahydropyrimidines to 4-Aminotetrahydropyrimidine 3-Oxides." ChemInform 25, no. 20 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199420072.

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34

Orelli, Liliana R., María B. García, Isabel A. Perillo, Loris Tonidandel, and Pietro Traldi. "A comparison of the electron ionization and electrospray behaviour of some N,N′-disubstituted hexahydropyrimidines." Rapid Communications in Mass Spectrometry 20, no. 5 (February 7, 2006): 823–28. http://dx.doi.org/10.1002/rcm.2375.

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35

Subramaniyan, Vasudevan, Ashok Kumar, Anbarasu Govindaraj, and Ganesan Mani. "Crystal structure and DFT analyses of a pentacoordinated PCP pincer nickel(II) complex." Acta Crystallographica Section C Structural Chemistry 75, no. 6 (May 21, 2019): 734–39. http://dx.doi.org/10.1107/s2053229619006211.

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Анотація:
The reaction of NiCl2 with 1,3-bis[(diphenylphosphanyl)methyl]hexahydropyrimidine in the presence of 2,6-dimethylphenyl isocyanide and KPF6 afforded a new pentacoordinated PCP pincer NiII complex, namely {1,3-bis[(diphenylphosphanyl)methyl]hexahydropyrimidin-2-yl-κN 2}(2,6-dimethylphenyl isocyanide-κC)nickel(II) hexafluoridophosphate 0.70-hydrate, [Ni(C9H9N)(C30H30ClN2P2)]PF6·0.7H2O or [NiCl{C(NCH2PPh2)2(CH2)3-κ3 P,C,P′}(Xylyl-NC)]PF6·0.7H2O, in very good yield. Its X-ray structure showed a distorted square-pyramidal geometry and the compound does not undergo dissociation in solution, as shown by variable-temperature NMR and UV–Vis studies. Density functional theory (DFT) calculations provided an insight into the bonding; the nickel dsp 2-hybridized orbitals form the basal plane and the nearly pure p orbital forms the axial bond. This is consistent with the NBO (natural bond orbital) analysis of analogous nickel(II) complexes.
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36

Kireeva, D. R., and A. I. Kamalova. "Synthesis of Hexahydropyrimidines and 1,2,3,4-Tetrahydropyridines by Reaction of Ethyl Benzoylacetate with Formaldehyde and Primary Amines." Russian Journal of Organic Chemistry 56, no. 10 (October 2020): 1733–37. http://dx.doi.org/10.1134/s1070428020100103.

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37

Berges, David A., Jianmei Fan, Sylvie Devinck, and Kendall Mower. "Preference for AxialN-Alkylation of Tetrahydro-1,3-oxazines and Hexahydropyrimidines: Manifestation of a Kinetic Anomeric Effect." Journal of Organic Chemistry 65, no. 3 (February 2000): 889–94. http://dx.doi.org/10.1021/jo991752i.

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38

Dandia, Anshu, Anuj K. Jain, and Sonam Sharma. "Indium triflate catalyzed one-pot multicomponent synthesis of spiro-hexahydropyrimidines explained by multiple covalent bond formation." Tetrahedron Letters 53, no. 39 (September 2012): 5270–74. http://dx.doi.org/10.1016/j.tetlet.2012.07.079.

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39

Maloshitskaya, Olga, Jari Sinkkonen, Vladimir V. Ovcharenko, Kirill N. Zelenin, and Kalevi Pihlaja. "Chain-ring-chain tautomerism in 2-aryl-substituted hexahydropyrimidines and 1H-2,3-dihydroperimidines. Does it appear?" Tetrahedron 60, no. 32 (August 2004): 6913–21. http://dx.doi.org/10.1016/j.tet.2004.05.092.

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40

Shephard, MJ, and MN Paddonrow. "A Caveat Concerning the Use of the AM1 and PM3 Semiempirical Methods in Calculating Conformational Preferences in Acyclic Amines and Saturated Azaheterocycles." Australian Journal of Chemistry 46, no. 4 (1993): 547. http://dx.doi.org/10.1071/ch9930547.

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Анотація:
A theoretical investigation of the conformational analysis of several acyclic amines, N- alkylated saturated azaheterocycles and alkylcyclohexanes (alkyl = Me, Et, isopropyl, t-butyl) has been carried out by using the MNDO, AM1 and PM3 semiempirical methods. It is found that all three methods correctly predict, qualitatively, the conformational preferences in alkylcyclohexanes, although the PM3 method underestimates the conformational energy for the t-butyl group by as much as 13 kJ/mol. Both AM1 and PM3 overestimate the conformational energy of the nitrogen lone pair to the extent that it exceeds that of the isopropyl group and (in the case of PM3) the t-butyl group, thereby leading to erroneous predictions of favoured conformations in amines and azaheterocycles . Thus, axial N-alkylpiperidines are predicted to be more stable than the equatorial conformers. Thus, application of the AM1 and PM3 methods to the conformational analysis of molecules containing amine functionalities is not recommended. Although the MNDO method gives a qualitative account of the conformational analysis of such molecules, with the exception of hexahydropyridazines and hexahydropyrimidines, the resulting conformational energies and molecular geometries are in poor agreement with experimental data.
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41

Besse, Richard, Peter J. Garratt, Christopher J. Hobbs, Helen M. Rogers, A. Mannan Sueleiman, Christopher S.J. Walpole, and Roger Wrigglesworth. "Ring size preference in the intramolecular cyclisation of amines with esters. Synthesis of aminoacid derived hexahydropyrimidines and tetrahydroimidazoles." Tetrahedron 46, no. 23 (January 1990): 7803–12. http://dx.doi.org/10.1016/s0040-4020(01)90077-8.

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42

Kar, Purabi, Aparajita Nayak, Y. P. Bhoi, and B. G. Mishra. "Preparation and catalytic application of sulfonated PVA-Zr-pillared clay nanocomposite materials towards one pot synthesis of hexahydropyrimidines." Microporous and Mesoporous Materials 223 (March 2016): 176–86. http://dx.doi.org/10.1016/j.micromeso.2015.11.006.

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BESSE, R., P. J. GARRATT, C. J. HOBBS, H. M. ROGERS, A. M. SUELEIMAN, C. S. J. WALPOLE, and R. WRIGGLESWORTH. "ChemInform Abstract: Ring Size Preference in the Intramolecular Cyclisation of Amines with Esters. Synthesis of Amino Acid Derived Hexahydropyrimidines and Tetrahydroimidazoles." ChemInform 22, no. 9 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199109085.

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Huang, Zhi-tang, and Zhi-rong Liu. "Synthesis of 2-(Benzoylmethylene)imidazolidines and -hexahydropyrimidines by Condensation of Ethyl Benzoylacetimidates With 1,2-Ethanediamine or 1,3-Propandiamine, and Some Addition Reactions." Synthesis 1987, no. 04 (1987): 357–62. http://dx.doi.org/10.1055/s-1987-27942.

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