Synthesis and Conformational Analysis of Naphthoxazine-Fused Phenanthrene Derivatives
Abstract
:1. Introduction
2. Results
2.1. Synthesis
2.2. Structural and Conformational Analysis
2.3. Detailed NMR Analysis of New Phenanthr[9,10-e]Oxazine 16
2.4. Detailed NMR Analysis of New Phenanthr[9,10-e]Oxazines 27a,b−28a,b
3. Materials and Methods
3.1. General Methods
3.2. Procedures
3.2.1. General Procedure for the Synthesis of Hydroxyphenanthryl-Isoquinoline, -Thienopyridine and -β-Carboline (3, 5 and 7)
3.2.2. General Procedure for the Synthesis of Phenanthr[9,10-e][1,3]Oxazinoisoquinoline,-Thienopyridine and -β-Carboline (8–10)
3.2.3. General Procedure for the Synthesis of Phenanthr[9,10-e][1,3]Oxazines (14, 15 and 16)
3.2.4. General Procedure for the Synthesis of Phenanthr[9,10-e][1,3]Oxazines (24, 26 and 28)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are not available. |
Products | Type of Heating | Solvent | Reaction Time | Temperature | Yield (%) |
---|---|---|---|---|---|
3 | Oil bath | - | 120 min | 80 °C | 10 |
Oil bath | - | 60 min | 100 °C | 19 | |
Oil bath | Acetonitrile | 60 min | 90 °C | 49 | |
MW | Acetonitrile | 10 min | 100 °C | 67 | |
MW | Acetonitrile | 20 min | 100 °C | 82 | |
5 | MW | Acetonitrile | 20 min | 100 °C | 72 |
MW | Acetonitrile | 35 min | 100 °C | 92 | |
7 | MW | Acetonitrile | 20 min | 100 °C | 63 |
MW | Acetonitrile | 40 min | 100 °C | 76 |
Product | Reaction Time | Temperature (°C) | Yield (%) |
---|---|---|---|
14 | 15 min | 60 | 47 |
80 | 86 | ||
100 | 29 | ||
15 | 15 min | 60 | 52 |
80 | 94 | ||
100 | 37 | ||
16 | 15 min | 60 | 21 |
80 | 76 | ||
100 | 32 |
Products | Reaction Time | Temperature (°C) | Yield (%) |
---|---|---|---|
23a,b 24a,b | 15 min | 60 | 48 |
80 | 85 | ||
100 | 33 | ||
25a,b 26a,b | 15 min | 60 | 28 |
80 | 78 | ||
100 | 19 | ||
27a,b 28a,b | 15 min | 60 | 51 |
80 | 93 | ||
100 | 38 |
Positions | 1/18 | 9a/18 | 18/16 (ř-eq) | 9a/16 (ř-eq) | 9a/16 (ř-ax) | 9a/10 | 14/15 (ř-ax) | 14/15 (ř-eq) |
---|---|---|---|---|---|---|---|---|
Measured NOE | strong | medium | strong | weak | weak | medium | weak | medium |
Calculated distances d [Ĺ] | 2.2 2.2(cis) | 3.6 2.7(cis) | 2.2 2.7(cis) | 4.1 3.8(cis) | 3.8 2.7(cis) | 2.8 3.0(cis) | 4.3 3.4(cis) | 2.9 2.9(cis) |
NOE-estimated distances d [Ĺ] | 2.2 | 3.4 | 2.3 | 4.4 | 4.3 | 2.8 | 3.5 | 3.0 |
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Belasri, K.; Topal, L.; Heydenreich, M.; Koch, A.; Kleinpeter, E.; Fülöp, F.; Szatmári, I. Synthesis and Conformational Analysis of Naphthoxazine-Fused Phenanthrene Derivatives. Molecules 2020, 25, 2524. https://doi.org/10.3390/molecules25112524
Belasri K, Topal L, Heydenreich M, Koch A, Kleinpeter E, Fülöp F, Szatmári I. Synthesis and Conformational Analysis of Naphthoxazine-Fused Phenanthrene Derivatives. Molecules. 2020; 25(11):2524. https://doi.org/10.3390/molecules25112524
Chicago/Turabian StyleBelasri, Khadija, Leila Topal, Matthias Heydenreich, Andreas Koch, Erich Kleinpeter, Ferenc Fülöp, and István Szatmári. 2020. "Synthesis and Conformational Analysis of Naphthoxazine-Fused Phenanthrene Derivatives" Molecules 25, no. 11: 2524. https://doi.org/10.3390/molecules25112524