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In the present work, a novel imidazole-core-based bisphenol (IBP) was synthesized and characterized. The IBP and formaldehyde were reacted separately with aniline and N,N-dimethylaminopropylamine (DMAPA) under appropriate conditions to obtain benzoxazines, which were characterized for their molecular structure and thermal behavior using different analytical methods. Both types of benzoxazines, imidazole core–aniline-based benzoxazines (IBPA-Bz) and imidazole core–DMAPA-based benzoxazines (IBPD-Bz), possess better glass temperatures (Tg) and higher char yields than conventional benzoxazines (bisphenol-F-based benzoxazine (BPFb) and bisphenol-A-based benzoxazine (BPAb)). However, the curing temperature (Tp) of IBPD-Bz is lower than that of IBPA-Bz. The blending of IBPA-Bz with conventional benzoxazines (BPAb and BPFb) improved their thermal stability to an appreciable extent. Furthermore, the addition of bismaleimide cross-linkers (4,4′-diaminodiphenylsulfone- and 4,4′-diaminodiphenylmethane-based bismaleimides) to the blends of IBPA-Bz and conventional benzoxazines improved the thermal behavior according to their nature and concentration. Moreover, the selected blends of benzoxazines were incorporated with 10% loadings of catalysts (4-hydroxyphenylmaleimide, 4-aminophenol, and 4-hydroxyacetophenone), and it was observed that Tpwas reduced without significant variation in the thermal behavior, i.e., a reduction of more than 35 °C was noticed for both conventional benzoxazines. On the basis of the data obtained from the different studies, it is concluded that the blends of IBPA-Bz and conventional benzoxazines can be used in the form of sealants, encapsulants, adhesives, and matrixes in the fields of microelectronic and automobile applications for better performance with enhanced longevity.