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Chemistry

Cercosporin-Photocatalyzed [4+1]- ve [4+2]-Hafif Koşullarda Azoalkenlerin Annülasyonları

Published: July 17, 2020
doi:
10.3791/60786
, , , , , ,
1Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology,Jiangnan University, 2School of Pharmaceutical Science,Jiangnan University

Summary

Metaliçermeyen fotokatalizör olarak cercosporin kullanan azot içeren heterodöngülerin sentezi için yeni rotalar geliştirilmiştir.

Abstract

Azot içeren heterocyclelara olan ilgi, yeni uyuşturucular için önemli motifler olduğu için sentetik toplumda hızla genişlemiştir. Geleneksel olarak termal sikloek reaksiyonları ile sentezlenirken, günümüzde hafif ve verimli koşullar nedeniyle fotokataliz tercih edilmektedir. Bu odak ile, azot içeren heterocycles sentezi için yeni bir fotokatalitik yöntem son derece istenir. Burada, cercosporin biyosentezi için bir protokol rapor ediyoruz, metalsiz fotokatalizör işlevi görebilen. Daha sonra azot içeren heterosiklasyon 1,2,3-tiaydiazollerin KSCN ile azoalkenlerin annülasyonu ile sentezi için cercosporin-fotokatalize protokolleri ve 1,4,5,6-tetrahidropirridazinsentezi [4+2] hafif koşullarda azoalkenlerin siklodimerizasyonu ile, sırasıyla. Sonuç olarak, mikrobiyal fermantasyon yöntemi ile organik sentez arasında hafif, uygun maliyetli, çevre dostu ve sürdürülebilir bir şekilde yeni bir köprü bulunmaktadır.

Introduction

Azot içeren heterocycles biyoaktivite ile doğal ürünlerin geniş bir yelpazede için sadece önemli iskeletler değil, aynı zamanda tarımsal kimyasallar ve uyuşturucu molekülleri için sentetik öncüleri1,2çünkü çok dikkat çekmiştir. Çeşitli N-heterocycles arasında, 1,2,3-tiaydiazoles3,4 ve 1,4,5,6-tetrahidropyridazines5,6 sentetik kimya çok yönlü ara olarak kullanılan en önemli moleküllerdir ( Şekil1). Fonksiyonel gruplarının modifikasyonu her zaman farklı farmakolojik aktiviteleri tetiklediğinden, azot içeren heterodöngülerin sentezi için etkili stratejiler geliştirmeye yönelik geniş çabalar gösterilmiştir ve çoğunlukla termal sikloek reaksiyonları7,8,9,10ile sentezlenmiştir. Günümüzde, sürdürülebilir kalkınma ve yeşil kimya gereksinimlerini karşılamak için, fotokataliz büyük önem ve avantajları11,,12,13,14, etkinliğini içeren 15 ,16,16,17,18,19 ve aktivasyon için stokiyometrik reaktifler kaçınma20,21uyguladı . Güçlü ve çok yönlü dört üniteli ara, azoalkenes (1,2-diaza-1,3-dienes)22,23,24,25,26,27,28,29, metal tabanlı Ru öncüsü olarak istihdam edilmiştir (bpy)3Cl2-fotokatalized reaksiyonlar halojen hidratozizin ve ketoyls annülasyonu için yüksek verimlilik ile .30 Ayrıca, aynı zamanda metal içermeyen Eosin Y fotokatalized sisteminde kullanılan, ancak sadece% 7 verim istenilen ürün göze. Metaliçermeyen fotokatalizatörler geçiş metal bazlı fotokatalizörler üzerinde büyük avantaj göstermek yana, çevresel faktör yanı sıra ucuz fiyatlar ile ilgili18,19, N-heterocycles sentezi için yeni metal içermeyen fotokatalitik sistemler geliştirmek son derece önemlidir.

Cercosporin31, 32,33,,3434,35, hipokrellin36,37,38,39,40, elsinokrom41 ve fleikrom42,43 ( Şekil2) doğada perilenequinonoid pigmentlere (PQPs) ait ve endofitik mantarlar tarafından üretilir, fotofizik ve fotobiyolojik özellikleri ile ilgili olarak yaygın olarak araştırılan ve fotodinamik tedavi ve fotofizik tanıda uygulanan, UV-vis bölgesinde güçlü emilimleri ve fotoensitizasyonun eşsiz özellikleri nedeniyle36,44,45,46,47. Işınlama üzerine, bu PQPs heyecanlı devlet ve daha sonra enerji transferi (EnT) ve elektron transferi (ET)35,38,44,48,49,50,51,52,53,54ile aktif türler oluşturmak istenebilir. Böylece, bu doğal PQPs nadiren 55,56 ,,57,,565858,59araştırılmıştır organik reaksiyonlar, sürücü için “metal-free” photocatalysts olarak kullanılabilir öngörülen .

Burada, servosporin in sivi fermantasyondan biyosentezine yönelik protokolü rapor ediyoruz ve daha sonra azoalkenler ve KSCN’nin [4+1] annülasyon reaksiyonu için metalsiz fotokatalizör olarak uyguluyoruz. [4+2] azoalkenlerin siklodimerizasyonu, sırasıyla hafif koşullarda 1,2,3-tiaydiazoz ve 1,4,5,6- tetrahidroridazinler yüksek verimlidir (Şekil 3).

Protocol

NOT: α-Halo-N-acyl-hidrazlar yayınlanmış bir prosedüre göre hazırlanmıştır60. Tüm çözücüler ve diğer kimyasal reaktifler daha fazla saflaştırma yapılmadan ticari kaynaklardan elde edilebildi. İlk olarak α-Halo-NN-ayl-hidratların sentezini ve cercosporin biyosentezini metalsiz fotokatalizör olarak tanımladık. Daha sonra, 1,2,3-tiaydiazol ve 1,4,5,6-tetrahidropiriridazin sentezi için cercosporin-fotokatalizreaksiyonların protokollerini g…

Representative Results

α-Halo-N-asil-hidrazsentezi: Protokol 1’e göre sentezlenirler. Cercosporin sentezi: Protokol 2’ye göre sentezlendi ve saflaştırılmıştı. 1.1.2 H NMR (400 MHz, CDCl3): δ ppm 14.82 (s, 2H, ArH), 7.06 (s, 2H, ArH), 5,57 (s, 2H, CH2), 4.20 (s, 6H, 2OCH3),3.62-3.57 (m, 2H, CH2), 3.42-3.37 (m, 2H, CH2),2.93-2…

Discussion

Azot içeren heterocyclelar birçok yeni ilaç için önemli motiflerdir ve geleneksel olarak termal sikloekleme reaksiyonları ile sentezlenirler. Büyük ilgi nedeniyle, bu bileşiklerin sentezi için yeni bir fotokatalitik yöntem son derece istenir. Cercosporin’in mükemmel fotosensitizasyon özelliklerinden yararlanmak için, azot içeren heterocycleları sentezlemek için iki kategoride metalsiz fotokatalizör olarak cercosporin uyguladık.

İlk olarak, standart koşullar altında KSCN i…

Disclosures

The authors have nothing to disclose.

Acknowledgements

Çin Ulusal Anahtar Ar-Ge Programı (2018YFA0901700), Jiangsu Eyaleti Doğa Bilimleri Vakfı (Hibe No. BK20160167, Bin Yetenek Planı (Genç Profesyoneller), Merkez Üniversiteler için Temel Araştırma Fonları (JUSRP51712B), Ulusal Birinci Sınıf Hafif Sanayi Teknolojisi ve Mühendisliği Disiplin Programı (LITE2018-14) ve Jiangsu Eyaleti Doktora Sonrası Vakfı (2018K153C) finansman desteği için.

Materials

2,4'-Dibromoacetophenone ENERGY D0500850050
2'-bromo-4-chloroacetophenone ENERGY A0500400050
2-Bromo-4'-fluoroacetophenone ENERGY A050037-5g
2-Bromoacetophenone ENERGY A0500870050
4-Bromobenzhydrazide ENERGY B0103390010
4-Chlorobenzhydrazide ENERGY D0511130050
4-Fluorobenzhydrazide ENERGY B010461-5g
5 W blue LED PHILIPS 29237328756
Benzoyl hydrazine ENERGY D0500610250
CH2Cl2 SINOPHARM 80047360
CH3CN SINOPHARM S3485101
CH3OH SINOPHARM 100141190
Cs2CO3 ENERGY E060058-25g
Ethyl acetate SINOPHARM 40065986
freeze dryer LABCONCO 7934074
HPLC Agilent 1260 Infinity II
KSCN ENERGY E0104021000
Na2SO4 SINOPHARM 51024461
organic microfiltration membrane SINOPHARM 92412511
S-7 medium Gluose 1g; Fructose 3g; Sucrose 6g; Sodium acetate 1g; Soytone 1g; Phenylalanine 5mg; Sodium benzoate 100mg; 1M KH2P04 buffer ph6.8; Biotin 1mg; Ca(NO3)2 6.5mg; Pyridoxal 1mg; Calcium pantothenate 1mg; Thiamine 1mg; MnCl2 5mg; FeCl3 2mg; Cu(NO3)2 1mg; MgSO4 3.6mg; ZnSO4 2.5mg
Schlenk tub Synthware F891910
sephadex LH-20 column GE 17009001
shaker Lab Tools BSH00847
silica gel ENERGY E011242-1kg
tBuOK ENERGY E0610551000
vacuum bump Greatwall SHB-III
vacuum evaporator
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Tags

CercosporinPhotocatalysis[4+1]-annulation[4+2]-annulationNitrogen-containing HeterocyclesAlpha-Halo-N-acyl-hydrazoneMicrobial Fermentation123-thiadiazole

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Icyishaka, P., Li, C., Lu, L., Bao, W., Li, J., Zhang, Y., Rao, Y. Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions. J. Vis. Exp. (161), e60786, doi:10.3791/60786 (2020).
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