According to the Primary Chronicle, Vladimir the Great rejected Judaism in 987 with the rationale that they lost Jerusalem. When Constantinople was conquered in 1453 by the Ottomans, was there any serious self-reflection on whether to re-evaluate Judaism or Orthodox Christianity in light of those grounds?
First of all, at least a part of the reason for rejecting Judaism (and Islam) was circumcision. What the Chronicles say is not perfectly reliable.
But, mostly, changing the state religion is a major revolution. One would not undertake that based on such a minor event as a fall of a neighbor. (cf. Raskol, when a relatively minor changes in the mid-17th century led to a long-term schism). In fact, as far as Russia was concerned, the fall of Constantinople was an opportunity to become the sole leader of the Orthodoxy ("3rd Rome").
Note also that the status of Jerusalem in Judaism is vastly different from that of Constantinople/Rome in Christianity.
Actually there were such considerations, not in the sense of changing to Islam but in the sense of changing to Catholicism.
As you know, Greeks before the fall of Constantinople signed an Unia document subscribing to Catholicism while keeping their rites unchanged so to obtain military support from the West (and that decision was controversial). This was the origin of the Byzantine rite Greek Catholic churches (the Uniates). Emperor John VIII even visited Rome.
But the military support, while existed, was insufficient, the Unia sparked internal opposition so that some viewed the Unia as an apostacy that led to the defeat.
That said, in Russia since then there was always a strong pro-Catholic party that was supported by the neighbouring Poland. In Western Ukraine, the Uniates became the dominant religion. And there were attempts to install Catholicism in Moscow, for instance by False Dmitry I who converted to Catholicism in 1604.
At the same time this development led to the consolidation of the nationalists around Orthodoxy as sympathies to Catholicism were seen as unpatriotic and pro-Polish.