  Let $p$ be a prime. We prove that certain amalgamated free pro-$p$ products
of Demushkin groups with pro-$p$-cyclic amalgam cannot give rise to a
1-cyclotomic oriented pro-$p$ group, and thus do not occur as maximal pro-$p$
Galois groups of fields containing a root of 1 of order $p$. We show that other
cohomological obstructions which are used to detect pro-$p$ groups that are not
maximal pro-$p$ Galois groups - the quadraticity of
$\mathbb{Z}/p\mathbb{Z}$-cohomology and the vanishing of Massey products - fail
with the above pro-$p$ groups. Finally, we prove that the Mina\v{c}-T\^an
pro-$p$ group cannot give rise to a 1-cyclotomic oriented pro-$p$ group, and we
conjecture that every 1-cyclotomic oriented pro-$p$ group satisfy the strong
$n$-Massey vanishing property for $n>2$.
