Organocatalytic Domino Knoevenagel Hetero-Diels-Alder Reaction for the Synthesis of Chromenopyran Derivatives

Title:Organocatalytic Domino Knoevenagel Hetero-Diels-Alder Reaction for the Synthesis of Chromenopyran Derivatives

Volume: 22 Issue: 1

Author(s): Sangepu Karthik, L. Vishnu Priya, B. Maheshwar Rao, D. R. Adarsh, B. Sridhar, B. V. Subba Reddy*Pannala Padmaja*

Affiliation:

• Centre for Semio Chemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India

• Centre for Semio Chemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India

Abstract: An organocatalytic, one-pot four-center two-component coupling reaction has been developed for the synthesis of tetrahydro-1H,7H-chromeno[3,4-c]chromen-1-one derivatives. The reaction proceeds smoothly in the presence of 5 mol% DL-Proline in methanol under reflux conditions. This method involves the Knoevenagel condensation of O-alkynyl tethered 2-hydroxybenzaldehydes with cyclic 1,3-diketones followed by an intramolecular hetero-Diels-Alder reaction. Novel classes of oxygen containing polycyclic frameworks are prepared in good yields by using this approach.

Cite this article as:

Karthik Sangepu, Priya L. Vishnu, Rao Maheshwar B., Adarsh D. R., Sridhar B., Subba Reddy B. V.*, Padmaja Pannala*, Organocatalytic Domino Knoevenagel Hetero-Diels-Alder Reaction for the Synthesis of Chromenopyran Derivatives, Letters in Organic Chemistry 2025; 22 (1) . https://dx.doi.org/10.2174/0115701786312736240604093915