Synthesis ( IF 2.2 ) Pub Date : 2018-11-07 , DOI: 10.1055/s-0037-1611279 Serge Thorimbert 1 , Candice Botuha 1 , Kevin Passador
Abstract
William Pitt and co-workers have created a virtual exploratory heterocyclic library ‘VEHICLe’ containing over 200 unconquered bicyclic heteroaromatic rings, synthetically feasible with potential medicinal interest. Since the publication of the 22 ‘heteroaromatic rings of the future’ by Pitt in 2009, 15 of them have been successfully synthesized as bicyclic or polycyclic forms and evaluated for applications in both biology and material science. This short review presents the critical synthesis associated with innovative synthetic methodologies of the synthetically conquered ring scaffolds from the list of 22 with a spotlight on the scientific contribution of this fascinating article for the expansion of the chemical diversity.
1 Introduction
2 Heteroaromatic Rings of the Future: The Synthetic challenge?
2.1 4-Pyrido[1,3]oxazin-4-one-P1
2.2 Pyrrolo[2,1-b][1,3]oxazin-4-one-P4
2.3 Furo[2,1-e]pyridazin-4(1H)-one-P5
2.4 Isoxazolo[3,4-c]pyridin-7-one-P6
2.5 5H,6H-[1,2]Thiazolo[5,4-c]pyridin-5-one-P7
2.6 4H,5H-Furo[3,2-b]pyridin-5-one-P8
2.7 1H,5H,6H-Pyrazolo[3,4-c]pyridin-5-one-P9
2.8 Thieno[3,4-c]pyridazine-P10
2.9 Pyrrolo[1,2-c][1,2,3]triazine-P11
2.10 Thieno[3,4-a]oxazole-P12
2.11 2,4-Dihydropyrrolo[3,2-c]pyrazole-P13
2.12 Pyrazolo[1,5-b]isoxazole-P14
2.13 Imidazo[1,5-c]pyrimidin-3(2H)-one-P16
2.14 Cyclopenta[b][1,4]oxazin-5(4H)-one-P17
2.15 2,3-Dihydro-2,6-naphthyridin-3-one-P18
3 Conclusion
William Pitt and co-workers have created a virtual exploratory heterocyclic library ‘VEHICLe’ containing over 200 unconquered bicyclic heteroaromatic rings, synthetically feasible with potential medicinal interest. Since the publication of the 22 ‘heteroaromatic rings of the future’ by Pitt in 2009, 15 of them have been successfully synthesized as bicyclic or polycyclic forms and evaluated for applications in both biology and material science. This short review presents the critical synthesis associated with innovative synthetic methodologies of the synthetically conquered ring scaffolds from the list of 22 with a spotlight on the scientific contribution of this fascinating article for the expansion of the chemical diversity.
1 Introduction
2 Heteroaromatic Rings of the Future: The Synthetic challenge?
2.1 4-Pyrido[1,3]oxazin-4-one-P1
2.2 Pyrrolo[2,1-b][1,3]oxazin-4-one-P4
2.3 Furo[2,1-e]pyridazin-4(1H)-one-P5
2.4 Isoxazolo[3,4-c]pyridin-7-one-P6
2.5 5H,6H-[1,2]Thiazolo[5,4-c]pyridin-5-one-P7
2.6 4H,5H-Furo[3,2-b]pyridin-5-one-P8
2.7 1H,5H,6H-Pyrazolo[3,4-c]pyridin-5-one-P9
2.8 Thieno[3,4-c]pyridazine-P10
2.9 Pyrrolo[1,2-c][1,2,3]triazine-P11
2.10 Thieno[3,4-a]oxazole-P12
2.11 2,4-Dihydropyrrolo[3,2-c]pyrazole-P13
2.12 Pyrazolo[1,5-b]isoxazole-P14
2.13 Imidazo[1,5-c]pyrimidin-3(2H)-one-P16
2.14 Cyclopenta[b][1,4]oxazin-5(4H)-one-P17
2.15 2,3-Dihydro-2,6-naphthyridin-3-one-P18
3 Conclusion
中文翻译:
“未来的杂芳族环”:探索不可征服的化学空间
摘要
威廉·皮特(William Pitt)和他的同事们创建了一个虚拟的探索性杂环库'VEHICLe',其中包含200多个未征服的双环杂芳族环,在合成上具有潜在的医学价值。自2009年皮特(Pitt)发表22个“未来的杂芳环”以来,其中15个已成功合成为双环或多环形式,并已在生物学和材料科学领域进行了评估。这篇简短的综述介绍了与22名单中被征服的环骨架的创新合成方法有关的关键合成方法,重点介绍了该引人入胜的文章对扩大化学多样性的科学贡献。
1引言
2未来的杂芳族环:合成挑战?
2.1 4-Pyrido [1,3]恶嗪-4-one- P1
2.2 Pyrrolo [2,1- b ] [1,3]恶嗪-4-one- P4
2.3呋喃[ 2,1 - e ]哒嗪-4(1 H)-one- P5
2.4异恶唑[3,4- c ]吡啶-7-一-P6
2.5 5 H,6 H- [1,2]噻唑并[5,4 - c ]吡啶-5-一-P7
2.6 4 ħ,5 ħ -呋喃并[3,2- b ]吡啶-5-酮- P8
2.7 1 ħ,5 ħ,6 ħ -吡唑并[3,4- c ^ ]吡啶-5-酮- P9
2.8噻吩并[3,4- c ^ ]哒嗪P10
2.9吡咯并[1,2 Ç ] [1,2,3]三嗪P11
2.10噻吩并[3,4- a ]恶唑-P12
2.11 2,4-二氢吡咯并[3,2- c ]吡唑-P13
2.12吡唑并[1,5- b ]异恶唑-P14
2.13咪唑并[1,5- c ]嘧啶-3(2 H)-one- P16
2.14环戊[ b ] [1,4]恶嗪-5(4 H)-one- P17
2.15 2,3-二氢-2,6-萘啶-3-一-P18
3结论
威廉·皮特(William Pitt)和他的同事们创建了一个虚拟的探索性杂环库'VEHICLe',其中包含200多个未征服的双环杂芳族环,在合成上具有潜在的医学价值。自2009年皮特(Pitt)发表22个“未来的杂芳环”以来,其中15个已成功合成为双环或多环形式,并已在生物学和材料科学领域进行了评估。这篇简短的综述介绍了与22名单中被征服的环骨架的创新合成方法有关的关键合成方法,重点介绍了该引人入胜的文章对扩大化学多样性的科学贡献。
1引言
2未来的杂芳族环:合成挑战?
2.1 4-Pyrido [1,3]恶嗪-4-one- P1
2.2 Pyrrolo [2,1- b ] [1,3]恶嗪-4-one- P4
2.3呋喃[ 2,1 - e ]哒嗪-4(1 H)-one- P5
2.4异恶唑[3,4- c ]吡啶-7-一-P6
2.5 5 H,6 H- [1,2]噻唑并[5,4 - c ]吡啶-5-一-P7
2.6 4 ħ,5 ħ -呋喃并[3,2- b ]吡啶-5-酮- P8
2.7 1 ħ,5 ħ,6 ħ -吡唑并[3,4- c ^ ]吡啶-5-酮- P9
2.8噻吩并[3,4- c ^ ]哒嗪P10
2.9吡咯并[1,2 Ç ] [1,2,3]三嗪P11
2.10噻吩并[3,4- a ]恶唑-P12
2.11 2,4-二氢吡咯并[3,2- c ]吡唑-P13
2.12吡唑并[1,5- b ]异恶唑-P14
2.13咪唑并[1,5- c ]嘧啶-3(2 H)-one- P16
2.14环戊[ b ] [1,4]恶嗪-5(4 H)-one- P17
2.15 2,3-二氢-2,6-萘啶-3-一-P18
3结论