Synthesis of novel symmetrical macrocycle via oxidative homocoupling of bisalkyne

Nurulain Kamalulazmy, Nurul Izzaty Hassan

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Abstract

A novel symmetrical macrocycle has been synthesised via oxidative homocoupling of bisalkyne, diprop-2-ynyl pyridine-2,6-dicarboxylate mediated by copper (I) iodide (CuI) and 4-dimethylaminopyridine (DMAP). The precursor compound was synthesised from 2,6-pyridine dicarbonyl dichloride and propargyl alcohol in the presence of triethylamine. The reaction mixture was stirred overnight and further purified via column chromatograpy with 76% yield. Single crystal for X-ray study was obtained by recrystallization from acetone. Subsequently, a symmetrical macrocycle was synthesised from oxidative homocoupling of precursor compound in open atmosphere. The crude product was purified by column chromatography to furnish macrocycle compound with 5% yield. Both compounds were characterised by IR, 1 H and 13 C NMR and mass spectral techniques. The unusual conformation of the bisalkyne and twisted conformation of designed macrocycle has influence the percentage yield. This has been studied thoroughly by Xray crystallography and electronic structure calculations.

Original languageEnglish
Title of host publication2014 UKM FST Postgraduate Colloquium - Proceedings of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology 2014 Postgraduate Colloquium
EditorsZahari Ibrahim, Haja Maideen Kader Maideen, Nazlina Ibrahim, Nurul Huda Abd Karim, Taufik Yusof, Fatimah Abdul Razak, Nurulkamal Maseran, Rozida Mohd Khalid, Noor Baa'yah Ibrahim, Hasidah Mohd. Sidek, Mohd Salmi Md Noorani, Norbert Simon
PublisherAmerican Institute of Physics Inc.
Pages309-312
Number of pages4
ISBN (Electronic)9780735412507
DOIs
Publication statusPublished - 1 Jan 2014
Event2014 Postgraduate Colloquium of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology, UKM FST 2014 - Selangor, Malaysia
Duration: 9 Apr 201411 Apr 2014

Publication series

NameAIP Conference Proceedings
Volume1614
ISSN (Print)0094-243X
ISSN (Electronic)1551-7616

Other

Other2014 Postgraduate Colloquium of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology, UKM FST 2014
CountryMalaysia
CitySelangor
Period9/4/1411/4/14

Fingerprint

pyridines
synthesis
dichlorides
chromatography
iodides
acetone
crystallography
alcohols
electronic structure
atmospheres
copper
nuclear magnetic resonance
single crystals
products
x rays

Keywords

  • Bisalkyne
  • Oxidative homocoupling
  • Symmetrical macrocycle

ASJC Scopus subject areas

  • Physics and Astronomy(all)

Cite this

Kamalulazmy, N., & Hassan, N. I. (2014). Synthesis of novel symmetrical macrocycle via oxidative homocoupling of bisalkyne. In Z. Ibrahim, H. M. K. Maideen, N. Ibrahim, N. H. A. Karim, T. Yusof, F. A. Razak, N. Maseran, R. M. Khalid, N. B. Ibrahim, H. M. Sidek, M. S. M. Noorani, ... N. Simon (Eds.), 2014 UKM FST Postgraduate Colloquium - Proceedings of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology 2014 Postgraduate Colloquium (pp. 309-312). (AIP Conference Proceedings; Vol. 1614). American Institute of Physics Inc.. https://doi.org/10.1063/1.4895213

Synthesis of novel symmetrical macrocycle via oxidative homocoupling of bisalkyne. / Kamalulazmy, Nurulain; Hassan, Nurul Izzaty.

2014 UKM FST Postgraduate Colloquium - Proceedings of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology 2014 Postgraduate Colloquium. ed. / Zahari Ibrahim; Haja Maideen Kader Maideen; Nazlina Ibrahim; Nurul Huda Abd Karim; Taufik Yusof; Fatimah Abdul Razak; Nurulkamal Maseran; Rozida Mohd Khalid; Noor Baa'yah Ibrahim; Hasidah Mohd. Sidek; Mohd Salmi Md Noorani; Norbert Simon. American Institute of Physics Inc., 2014. p. 309-312 (AIP Conference Proceedings; Vol. 1614).

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Kamalulazmy, N & Hassan, NI 2014, Synthesis of novel symmetrical macrocycle via oxidative homocoupling of bisalkyne. in Z Ibrahim, HMK Maideen, N Ibrahim, NHA Karim, T Yusof, FA Razak, N Maseran, RM Khalid, NB Ibrahim, HM Sidek, MSM Noorani & N Simon (eds), 2014 UKM FST Postgraduate Colloquium - Proceedings of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology 2014 Postgraduate Colloquium. AIP Conference Proceedings, vol. 1614, American Institute of Physics Inc., pp. 309-312, 2014 Postgraduate Colloquium of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology, UKM FST 2014, Selangor, Malaysia, 9/4/14. https://doi.org/10.1063/1.4895213
Kamalulazmy N, Hassan NI. Synthesis of novel symmetrical macrocycle via oxidative homocoupling of bisalkyne. In Ibrahim Z, Maideen HMK, Ibrahim N, Karim NHA, Yusof T, Razak FA, Maseran N, Khalid RM, Ibrahim NB, Sidek HM, Noorani MSM, Simon N, editors, 2014 UKM FST Postgraduate Colloquium - Proceedings of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology 2014 Postgraduate Colloquium. American Institute of Physics Inc. 2014. p. 309-312. (AIP Conference Proceedings). https://doi.org/10.1063/1.4895213
Kamalulazmy, Nurulain ; Hassan, Nurul Izzaty. / Synthesis of novel symmetrical macrocycle via oxidative homocoupling of bisalkyne. 2014 UKM FST Postgraduate Colloquium - Proceedings of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology 2014 Postgraduate Colloquium. editor / Zahari Ibrahim ; Haja Maideen Kader Maideen ; Nazlina Ibrahim ; Nurul Huda Abd Karim ; Taufik Yusof ; Fatimah Abdul Razak ; Nurulkamal Maseran ; Rozida Mohd Khalid ; Noor Baa'yah Ibrahim ; Hasidah Mohd. Sidek ; Mohd Salmi Md Noorani ; Norbert Simon. American Institute of Physics Inc., 2014. pp. 309-312 (AIP Conference Proceedings).
@inproceedings{207d096ed30945239d8b89275ca268f3,
title = "Synthesis of novel symmetrical macrocycle via oxidative homocoupling of bisalkyne",
abstract = "A novel symmetrical macrocycle has been synthesised via oxidative homocoupling of bisalkyne, diprop-2-ynyl pyridine-2,6-dicarboxylate mediated by copper (I) iodide (CuI) and 4-dimethylaminopyridine (DMAP). The precursor compound was synthesised from 2,6-pyridine dicarbonyl dichloride and propargyl alcohol in the presence of triethylamine. The reaction mixture was stirred overnight and further purified via column chromatograpy with 76{\%} yield. Single crystal for X-ray study was obtained by recrystallization from acetone. Subsequently, a symmetrical macrocycle was synthesised from oxidative homocoupling of precursor compound in open atmosphere. The crude product was purified by column chromatography to furnish macrocycle compound with 5{\%} yield. Both compounds were characterised by IR, 1 H and 13 C NMR and mass spectral techniques. The unusual conformation of the bisalkyne and twisted conformation of designed macrocycle has influence the percentage yield. This has been studied thoroughly by Xray crystallography and electronic structure calculations.",
keywords = "Bisalkyne, Oxidative homocoupling, Symmetrical macrocycle",
author = "Nurulain Kamalulazmy and Hassan, {Nurul Izzaty}",
year = "2014",
month = "1",
day = "1",
doi = "10.1063/1.4895213",
language = "English",
series = "AIP Conference Proceedings",
publisher = "American Institute of Physics Inc.",
pages = "309--312",
editor = "Zahari Ibrahim and Maideen, {Haja Maideen Kader} and Nazlina Ibrahim and Karim, {Nurul Huda Abd} and Taufik Yusof and Razak, {Fatimah Abdul} and Nurulkamal Maseran and Khalid, {Rozida Mohd} and Ibrahim, {Noor Baa'yah} and Sidek, {Hasidah Mohd.} and Noorani, {Mohd Salmi Md} and Norbert Simon",
booktitle = "2014 UKM FST Postgraduate Colloquium - Proceedings of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology 2014 Postgraduate Colloquium",

}

TY - GEN

T1 - Synthesis of novel symmetrical macrocycle via oxidative homocoupling of bisalkyne

AU - Kamalulazmy, Nurulain

AU - Hassan, Nurul Izzaty

PY - 2014/1/1

Y1 - 2014/1/1

N2 - A novel symmetrical macrocycle has been synthesised via oxidative homocoupling of bisalkyne, diprop-2-ynyl pyridine-2,6-dicarboxylate mediated by copper (I) iodide (CuI) and 4-dimethylaminopyridine (DMAP). The precursor compound was synthesised from 2,6-pyridine dicarbonyl dichloride and propargyl alcohol in the presence of triethylamine. The reaction mixture was stirred overnight and further purified via column chromatograpy with 76% yield. Single crystal for X-ray study was obtained by recrystallization from acetone. Subsequently, a symmetrical macrocycle was synthesised from oxidative homocoupling of precursor compound in open atmosphere. The crude product was purified by column chromatography to furnish macrocycle compound with 5% yield. Both compounds were characterised by IR, 1 H and 13 C NMR and mass spectral techniques. The unusual conformation of the bisalkyne and twisted conformation of designed macrocycle has influence the percentage yield. This has been studied thoroughly by Xray crystallography and electronic structure calculations.

AB - A novel symmetrical macrocycle has been synthesised via oxidative homocoupling of bisalkyne, diprop-2-ynyl pyridine-2,6-dicarboxylate mediated by copper (I) iodide (CuI) and 4-dimethylaminopyridine (DMAP). The precursor compound was synthesised from 2,6-pyridine dicarbonyl dichloride and propargyl alcohol in the presence of triethylamine. The reaction mixture was stirred overnight and further purified via column chromatograpy with 76% yield. Single crystal for X-ray study was obtained by recrystallization from acetone. Subsequently, a symmetrical macrocycle was synthesised from oxidative homocoupling of precursor compound in open atmosphere. The crude product was purified by column chromatography to furnish macrocycle compound with 5% yield. Both compounds were characterised by IR, 1 H and 13 C NMR and mass spectral techniques. The unusual conformation of the bisalkyne and twisted conformation of designed macrocycle has influence the percentage yield. This has been studied thoroughly by Xray crystallography and electronic structure calculations.

KW - Bisalkyne

KW - Oxidative homocoupling

KW - Symmetrical macrocycle

UR - http://www.scopus.com/inward/record.url?scp=85063851972&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85063851972&partnerID=8YFLogxK

U2 - 10.1063/1.4895213

DO - 10.1063/1.4895213

M3 - Conference contribution

T3 - AIP Conference Proceedings

SP - 309

EP - 312

BT - 2014 UKM FST Postgraduate Colloquium - Proceedings of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology 2014 Postgraduate Colloquium

A2 - Ibrahim, Zahari

A2 - Maideen, Haja Maideen Kader

A2 - Ibrahim, Nazlina

A2 - Karim, Nurul Huda Abd

A2 - Yusof, Taufik

A2 - Razak, Fatimah Abdul

A2 - Maseran, Nurulkamal

A2 - Khalid, Rozida Mohd

A2 - Ibrahim, Noor Baa'yah

A2 - Sidek, Hasidah Mohd.

A2 - Noorani, Mohd Salmi Md

A2 - Simon, Norbert

PB - American Institute of Physics Inc.

ER -