A Project Report as a part of the requirement for the Degree of M.Sc. Chemistry

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Project under Dr. P. R. Sridhar Research Group

School of Chemistry

University of Hyderabad

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Introduction

3Shao, J.; Wanwan, Y.; Shao, Z.; Yongping, Y. Chem. Commun. 2012, 48, 2785-2787

• Heterocyclic compound have great important in pharmaceuticals as medicine.

• Synthesis some functional heterocyclic compound by simple, eco-friendly, and cost-effective method.

• Selecting solvent , water is a green solvent and has recently attracted considerable attentions. Many famous reaction such as Claisenrearrangement. Diels-Alder, Reformatsky, and pinacol-coupling reactions use water .

• PEG-400 has become an alternative reaction media to perform organic synthesis due to its inherent advantages over toxic solvents. Furthermore, PEG is inexpensive easy to handle, thermally stable, non-toxic and inexpensive.

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Hypothesis

Breslow, R. Acc. Chem. Res. 1991, 24, 159.

Hundreds of MCRs have been described over the years.

Special subclasses are isocyanides based MCRs (IMCRs). They are

particularly interesting because they are more versatile and diverse than

the remaining MCRs.

Today most MCRs chemistry performed with isoyanide relates to the

classical reactions of Passerini and Ugi.

.

Mario Passerini (1881-1962), the inventor of

the most significant isocyanide based MCRs

Picture taken from internet

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We synthesis some functionalized heterocyclic compounds with the use of PEG-400 as asolvent.The three components mixtures 2,6-lutidine, aldehyde and activated methyleneprecursor were mixed in 1.1:1:1.2 equivalents, respectively and transferred to a 25 mLround bottom flask containing 5 mL of polyethyleneglycol to serve as solvent.

The round bottom was stirred under reflux condition. The temperature was maintainedat 110 0C for 12 hr .

The progress of reaction was monitored by TLC using 30% ethyl acetate in hexane as amobile phase.

After completion of reaction the reaction mixture was cooled to room temperature.The reaction mixture was poured with water and ethyl acetate .

The organic layer was removed under reduced pressure. Lastly the mixture was purifiedby column chromatography on silica gel using ethyl acetate: hexane mixture .

PROCEDURE

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Scheme 1:

Synthesis of 2-(1-(4-bromophenyl)-2-(6-methylpyridin-2-yl)ethyl)malononitrile (4)

Scheme 2:

Synthesis of 2-(2-(6-methylpyridin-2-yl)-1-(3-nitrophenyl)ethyl)malononitrile (6)

Synthesis of ethyl 4-(6-methylpyridin-2-yl)-2-nitro-3-(4-nitrophenyl)butanoate(9)

Scheme 3:

Scheme 4:

Synthesis of 2-(1-(4-isopropylphenyl)-2-(6-methylpyridin-2-yl)ethyl)malononitrile (11)

When we check with more heat in short time, we did not get our product. It

shows that moderate temperature for long time is necessary for our method

of reaction.

We monitored the rate of reaction by TLC most of the compounds are active

in long ultra violet (365 nm) and some are iodine active.

All the synthesized compound shows satisfactory result with 1H-NMR and

13C NMR spectra which obtained on solution in CDCl3 using TMS as

internal standard.

RESULTS AND DISCUSSION

Dr. Perali Ramu Sridhar

Dean, School of Chemistry, UOH

All the Faculty, School of Chemistry, UOH

Ph.d scholars and friends.

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