Green Chemistry Metrics: Calculation of Green Chemistry Metrics of Biginelli Compounds Synthesized Under the Catalyst and Catalyst-Free Reaction Conditions

Öz

In this study, green chemistry metrics such as atom economy, environmental factor (E-factor), carbon efficieny, reaction mass efficiency and mass intensity of synthesized twelve Biginelli compounds under MgBr2 or MgCl2·6H2O catalysed, solvent-free and catalyst-free with solvent (EtOH) conditions were calculated. All green chemistry metrics results were compared and the best green chemistry reaction conditions and green metrics for twelve Biginelli compounds were determined.

Anahtar Kelimeler

• Green metrics,Atom economy,Environmental factor (E-factor),Carbon efficiency,Reaction mass efficiency,Biginelli Reaction

Yeşil Kimya Ölçümleri: Katalizörlü ve Katalizörsüz Reaksiyon Şartlarında Sentezlenmiş Biginelli Bileşiklerinin Yeşil Kimya Ölçümlerinin Hesaplanması

Öz

Bu çalışmada, MgBr2 veya MgCl2·6H2O katalizlenmiş, çözücüsüz ve katalizörsüz, çözücülü (EtOH) reaksiyon şartlarında sentezlenmiş oniki adet Biginelli bileşiğinin atom ekonomisi, çevresel etki faktörü (E-faktör), karbon etkinliği, reaksiyon kütle etkinliği ve kütle yoğunluğu gibi yeşil kimya ölçümleri hesaplanmıştır. Tüm yeşil kimya ölçüm sonuçları karşılaştırılmış ve oniki Biginelli bileşiği için en iyi yeşil kimya reaksiyon şartları ve yeşil ölçümler belirlenmiştir.

Anahtar Kelimeler

• Yeşil Kimya Ölçümleri,Atom Ekonomisi,Çevresel Etki Faktörü,Karbon Etkinliği,Reaksiyon Kütle etkinliği,Biginelli Reaksiyonu

Kaynakça

1. Biginelli, P. (1891a). Intorno ad uramidi aldeidiche dell’etere acetilacetico. Gazzetta chimica Italiana, 21, 337-340.
2. Biginelli, P. (1891b). Intorno ad uramidi aldeidiche dell’etere acetilacetico. Gazzetta chimica Italiana, 21, 455-461.
3. Biginelli, P. (1891c). Ueber Aldehyduramide des Acetessigäthers. Berichte der deutschen chemischen Gesellschaft, 24, 1317-1319.
4. Biginelli, P. (1891d). Ueber Aldehyduramide des Acetessigäthers. II. Berichte der deutschen chemischen Gesellschaft, 24, 2962-2967.
5. Biginelli, P. (1893). Aldehyde-urea derivatives of aceto- and oxaloacetic acids. Gazzetta chimica Italiana, 23, 360-413.
6. Atwal K. S., Rovnyak G. C., O'Reilly B. C., Schwartz J. (1989). Substituted 1,4-dihydropyrimidines. 3. Synthesis of selectively functionalized 2-hetero-1,4- dihydropyrimidines. Journal of Organic Chemistry, 54, 5898-5907. doi: 10.1021/jo00286a020
7. Atwal K.S., Rovnyak G. C., Kimball D., Floyd D. M., Moreland S., Swanson B. N., Gougoutas J. Z., Schwartz J., Smillie K. M., Malley M. F. (1990). Dihydropyrimidine calcium channel blockers. II. 3-Substituted-4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potent mimics of dihydropyridines. Journal of Medicinal Chemistry, 33, 2629-2635. doi: 10.1021/jm00167a035
8. Kappe C. O., Fabian W. M. F., Semones M. A. (1997). Conformational analysis of 4-aryl-dihydropyrimidine calcium channel modulators. A comparison of ab initio, semiempirical and X-Ray crystallographic studies. Tetrahedron, 53, 2803-2816. doi: 10.1016/S0040-4020(97)00022-7

9. Rovnyak G. C., Kimball S. D., Beyer B., Cucinotta G., DiMarco J. D., Gougoutas J., Hedberg A., Malley M., McCarthy J. P. (1995). Calcium entry blockers and activators: conformational and structural determinants of dihydropyrimidine calcium channel modulators. Journal of Medicinal Chemistry, 38,119-129. doi: 10.1021/jm00001a017
10. Anastas P. T., Warner J. C. (1998). Green Chemistry: Theory and Practice, Oxford University Press: New York, 30.
11. Constable, D. J. C., Curzons, A. D., Cunningham V.L. (2002). Metrics to ‘green’ chemistry- which are the best? Green Chemistry, 4, 521-527. doi: 10.1039/b206169b
12. Sheldon R. A. (2007). The E Factor: fifteen years on. Green Chemistry, 9, 1273-1283. doi: 10.1039/B713736M
13. Sheldon R. A. (2008). E factors, green chemistry and catalysis: an odyssey. Chemical Communications, 3352-3365. doi: 10.1039/B803584A
14. Trost B. M. (1991). The atom economy-a search for synthetic efficiency. Science, 254, 1471-1477.
15. Trost B. M. (1995). Atom Economy-A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the Way. Angewandte Chemie International Edition in English, 34, 259-281. doi: 10.1002/anie.199502591
16. Gülten. S. (2013). Magnesium bromide and magnesium chloride hexahydrate catalyzed one-pot synthesis of dihydropyrimidines via Biginelli reaction under solvent-free conditions. Journal of Heterocyclic Chemistry, 50, 391-395. doi: 10.1002/jhet.980