Transition-metal catalyzed reactions have brought a revolution in the field of organic synthesis. When reactive functionalities are created by organometallic reactions, new heterocyclic scaffolds can be synthesized in an excellent way. The most important part of these reaction is transition-metal catalyzed construction of a carbon-carbon as well as carbon-nitrogen bonds. The objective of this project was development of new synthetic methodologies leading to the formation of new heterocyclic compounds where alkyne cyclization was used as the major reaction without metal. We started from the simple starting materials; aromatic compounds bearing aldehyde and hydroxyl groups in the ortho-position. Two different alkyne functionalites were attached to the aromatic rings. First O-propargyl salicylaldehyde was synthesized. For incorporation of the second propargyl group, the appropriate compounds were reacted with propargylamine. The condensation between the amine functionality and carbonyl group resulted in the formation of imine derivatives with two propargyl groups in the same molecule. Under basic condition, the alkyne was rearranged to the corresponding allene, which is in conjugation with the imine functionality. Intramolecular [2+4] cycloaddition reaction gave the chromenopyridine derivatives. The general applicability of this reaction was shown with different substituted salicylaldehyde as well as with naphthalene ring.