Diastereoselective Synthesis of Fused Tricyclic Pyridopyrimidines via Tandem Cyclization of Allenoates and Cyclic Amidines.

The tandem cyclization of easily accessible allenoates and cyclic amidines for the synthesis of functionalized tricyclic pyridopyrimidines is reported herein. The annulation featured a broad substrate scope with good functional group tolerance under very mild conditions (35 examples, 32-85% yields). The pyridopyrimidines were obtained in a very short reaction time (1 min), at room temperature, under neat conditions, which offers an alternative way to the sustainable synthesis of functionalized pyridopyrimidines. The scalability of the developed protocol is further demonstrated by a gram-scale synthesis.

DBU-Catalyzed Diastereo/Regioselective Access to Highly Substituted Spiro-oxetane Oxindoles via Ring Annulation of Isatins and Allenoates.

A facile and efficient method for the diastereo/regioselective synthesis of highly functionalized spiro-oxetane oxindoles has been described. The 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed reaction proceeds via spiro-annulation of isatins and allenoates. The reaction is compatible with a wide range of isatins containing electron-donating groups (EDGs) and electron-withdrawing groups (EWGs) with various allenoates affording the corresponding products in acceptable yields. It is noteworthy that this is the first protocol for constructing structurally diverse motifs of highly functionalized spiro-oxetane oxindoles of pharmaceutical relevance.