Functionalized 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phenyl)prop-2-en-1-ones: Synthetic pathway, and the structures of six examples

N/ACitations
Citations of this article
16Readers
Mendeley users who have this article in their library.

Abstract

Five examples each of 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-[4-(prop-2-yn-1-yloxy)phenyl]prop-2-en-1-ones and the corresponding 1-(4-azidophenyl)-3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-ones have been synthesized in a highly efficient manner, starting from a common source precursor, and structures have been determined for three examples of each type. In each of 3-[5-(2-chlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl]-1-[4-(prop-2-yn-1-yloxy)phenyl]prop-2-en-1-one, C28H21ClN2O3, (Ib), the isomeric 3-[5-(2-chlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl]-1-[4-(prop-2-yn-1-yloxy)phenyl]prop-2-en-1-one, (Ic), and 3-[3-methyl-5-(naphthalen-2-yloxy)-1-phenyl-1H-pyrazol-4-yl]-1-[4-(prop-2-ynyloxy)phenyl]prop-2-en-1-one, C32H24N2O3, (Ie), the molecules are linked into chains of rings, formed by two independent C-H..O hydrogen bonds in (Ib) and by a combination of C-H..O and C-H..p(arene) hydrogen bonds in each of (Ic) and (Ie). There are no direction-specific intermolecular interactions in the structure of 1-(4-azidophenyl)-3-[3-methyl-5-(2-methylphenoxy)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one, C26H21N5O2, (IIa). In 1-(4-azidophenyl)-3-[5-(2,4-dichlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one, C25H17Cl2N5O2, (IId), the dichlorophenyl group is disordered over two sets of atomic sites having occupancies 0.55 14;(4) and 0.45 14;(4), and the molecules are linked by a single C-H..O hydrogen bond to form cyclic, centrosymmetric R 2 2(20) dimers. Similar dimers are formed in 1-(4-azidophenyl)-3-[3-methyl-5-(naphthalen-2-yloxy)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one, C29H21N5O2, (IIe), but here the dimers are linked into a chain of rings by two independent C-H.p(arene) hydrogen bonds. Comparisons are made between the molecular conformations within both series of compounds.

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Cite

CITATION STYLE

APA

Kumar, H. K., Yathirajan, H. S., Asm, Manju, N., Kalluray, B., Rathore, R. S., & Glidewell, C. (2020). Functionalized 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phenyl)prop-2-en-1-ones: Synthetic pathway, and the structures of six examples. Acta Crystallographica Section E: Crystallographic Communications, 76, 683–691. https://doi.org/10.1107/S2056989020005113

Readers over time

‘20‘21‘22‘23‘24‘2502468

Readers' Seniority

Tooltip

Professor / Associate Prof. 3

43%

Researcher 2

29%

Lecturer / Post doc 1

14%

PhD / Post grad / Masters / Doc 1

14%

Readers' Discipline

Tooltip

Medicine and Dentistry 4

50%

Chemistry 2

25%

Nursing and Health Professions 1

13%

Agricultural and Biological Sciences 1

13%

Save time finding and organizing research with Mendeley

Sign up for free
0