Pyrano and furanocoumarins are oxygen-containing heterocycles frequently found in natural products and biologically active molecules. In the present work, ninhydrin core is employed for the first time as the pivotal framework to construct benzopyrano/furano coumarin skeleton. It has been found that substrates like phenol, p-/m-cresol, m-methoxyphenol, p-chlorophenol etc. reacted with ninhydrin-4-hydroxycoumarin adduct 3 in AcOH/H2SO4 to furnish a new class of spiropyranocoumarins 5a-f via condensation/cyclization sequence. Under similar conditions, reaction of adduct 3 with 3,5-dihydroxybenzoic acid delivered benzofuranyl coumarin 6 through ring closing/ring opening mechanism. Structures of the synthesized compounds were characterized by IR, 1H and 13C NMR spectroscopy. Single crystal X-ray diffraction study revealed that spiropyranocoumarin 5b self-assembled to form sheet-like arrangement. However, benzofuranyl coumarin 6 was found to display helix-like architecture in the crystalline state. Scanning electron microscopy (SEM) images of compound 5b exhibited flat fibrillar morphology, whereas compound 6 revealed formation of vesicular structure. These types of small heterocyclic molecules are decent candidates for producing promising soft materials.