Applying Gewald reaction for the preparation of some novel aminothieno derivatives featuring noroxymorphone skeletal backbone

ABSTRACT

A group of noroxymorphone derivatives were subjected to Gewald reaction conditions to prepare their respective aminothieno products. In refluxing piperidine/ethanol, 1a–g reacted with elemental sulfur and malononitrile to produce 2a–g in high yields. Reactions took place in one pot and completed within 4–7 h and products precipitated spontaneously in the reaction mixtures.

GRAPHICAL ABSTRACT

KEYWORDS:

• Noroxymorphones
• aminothiophenes
• heterocycles
• multicomponent reaction
• Gewald reaction

Acknowledgement

S. B. would like to thank TEMAD Pharmaceutical Company for providing some of the required chemicals.

Disclosure statement

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

ORCID

Mohammad M. Mojtahedi http://orcid.org/0000-0002-0452-590X