Synthesis 2019; 51(02): 384-398
DOI: 10.1055/s-0037-1611279
short review
© Georg Thieme Verlag Stuttgart · New York

‘Heteroaromatic Rings of the Future’: Exploration of Unconquered Chemical Space

Kevin Passador
,
Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, IPCM, 4 place Jussieu, 75005 Paris, France   eMail: [email protected]   eMail: [email protected]
,
Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, IPCM, 4 place Jussieu, 75005 Paris, France   eMail: [email protected]   eMail: [email protected]
› Institutsangaben
This work was supported by the University Sorbonne Université (former University P. et M. Curie, UPMC) and CNRS for funding. The French Ministry of research and teaching fellowship (MENRT) is gratefully acknowledged for the Ph.D. grant to K.P.
Weitere Informationen

Publikationsverlauf

Received: 24. Juli 2018

Accepted after revision: 30. September 2018

Publikationsdatum:
07. November 2018 (online)


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

 
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