DFT Analysis and Synthesis of Medicinally Important Pyrrolo[2,3-d]Pyrimidines by Using Thiamine Hydrochloride as a Recyclable Organocatalyst in Aqueous Media

Abstract

A facile, environmentally benign and proficient route has been developed for the diverse synthesis of pyrrolo[2,3-d]pyrimidine derivatives followed by heterocyclization starting from Amino uracil, arylgyoxal and malononitrile/thiols. Readily available thiamin hydrochloride organocatalyst was used as a green promoting medium. As well as the reaction progress was taken place under aqueous media. This procedure also offers a base and metal free approach which endowed high yields with better functional group tolerating ability and mild reaction conditions. Further, methodology had a widescope with recyclability and reuse of thiamin hydrochloride. DFT/TD-DFT calculations with B3LYP/6-311G++ level of theory were used to study the optimized geometry and HOMO-LUMO energy of the synthesized compounds (4b and 6i).

Keywords:

• Environmentally benign
• green chemistry
• organocatalyst
• DFT
• pyrrolo[2,3-d] pyrimidines

Acknowledgements

The authors gratefully acknowledge SAIF, Punjab University Chandigarh for providing all the spectroscopic and analytical data. I also acknowledge Dr. Sonam Shakya, Department of Chemistry, Aligarh Muslim University for providing the DFT studies.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

M.D. Ansari acknowledges UGC, New Delhi for the financial support. Ankit Verma acknowledges UGC, New Delhi for the Senior Research Fellowship (SRF).