diff --git a/mypy/exprtotype.py b/mypy/exprtotype.py
index e0d2fe7835432..685e26e35b70a 100644
--- a/mypy/exprtotype.py
+++ b/mypy/exprtotype.py
@@ -4,14 +4,15 @@
 
 from mypy.nodes import (
     Expression, NameExpr, MemberExpr, IndexExpr, RefExpr, TupleExpr, IntExpr, FloatExpr, UnaryExpr,
-    ComplexExpr, ListExpr, StrExpr, BytesExpr, UnicodeExpr, EllipsisExpr, CallExpr,
+    ComplexExpr, ListExpr, StrExpr, BytesExpr, UnicodeExpr, EllipsisExpr, CallExpr, OpExpr,
     get_member_expr_fullname
 )
 from mypy.fastparse import parse_type_string
 from mypy.types import (
     Type, UnboundType, TypeList, EllipsisType, AnyType, CallableArgument, TypeOfAny,
-    RawExpressionType, ProperType
+    RawExpressionType, ProperType, UnionType
 )
+from mypy.options import Options
 
 
 class TypeTranslationError(Exception):
@@ -29,7 +30,9 @@ def _extract_argument_name(expr: Expression) -> Optional[str]:
         raise TypeTranslationError()
 
 
-def expr_to_unanalyzed_type(expr: Expression, _parent: Optional[Expression] = None) -> ProperType:
+def expr_to_unanalyzed_type(expr: Expression,
+                            options: Optional[Options] = None,
+                            _parent: Optional[Expression] = None) -> ProperType:
     """Translate an expression to the corresponding type.
 
     The result is not semantically analyzed. It can be UnboundType or TypeList.
@@ -53,7 +56,7 @@ def expr_to_unanalyzed_type(expr: Expression, _parent: Optional[Expression] = No
         else:
             raise TypeTranslationError()
     elif isinstance(expr, IndexExpr):
-        base = expr_to_unanalyzed_type(expr.base, expr)
+        base = expr_to_unanalyzed_type(expr.base, options, expr)
         if isinstance(base, UnboundType):
             if base.args:
                 raise TypeTranslationError()
@@ -69,14 +72,20 @@ def expr_to_unanalyzed_type(expr: Expression, _parent: Optional[Expression] = No
                 # of the Annotation definition and only returning the type information,
                 # losing all the annotations.
 
-                return expr_to_unanalyzed_type(args[0], expr)
+                return expr_to_unanalyzed_type(args[0], options, expr)
             else:
-                base.args = tuple(expr_to_unanalyzed_type(arg, expr) for arg in args)
+                base.args = tuple(expr_to_unanalyzed_type(arg, options, expr) for arg in args)
             if not base.args:
                 base.empty_tuple_index = True
             return base
         else:
             raise TypeTranslationError()
+    elif (isinstance(expr, OpExpr)
+          and expr.op == '|'
+          and options
+          and options.python_version >= (3, 10)):
+        return UnionType([expr_to_unanalyzed_type(expr.left, options),
+                          expr_to_unanalyzed_type(expr.right, options)])
     elif isinstance(expr, CallExpr) and isinstance(_parent, ListExpr):
         c = expr.callee
         names = []
@@ -109,19 +118,19 @@ def expr_to_unanalyzed_type(expr: Expression, _parent: Optional[Expression] = No
                     if typ is not default_type:
                         # Two types
                         raise TypeTranslationError()
-                    typ = expr_to_unanalyzed_type(arg, expr)
+                    typ = expr_to_unanalyzed_type(arg, options, expr)
                     continue
                 else:
                     raise TypeTranslationError()
             elif i == 0:
-                typ = expr_to_unanalyzed_type(arg, expr)
+                typ = expr_to_unanalyzed_type(arg, options, expr)
             elif i == 1:
                 name = _extract_argument_name(arg)
             else:
                 raise TypeTranslationError()
         return CallableArgument(typ, name, arg_const, expr.line, expr.column)
     elif isinstance(expr, ListExpr):
-        return TypeList([expr_to_unanalyzed_type(t, expr) for t in expr.items],
+        return TypeList([expr_to_unanalyzed_type(t, options, expr) for t in expr.items],
                         line=expr.line, column=expr.column)
     elif isinstance(expr, StrExpr):
         return parse_type_string(expr.value, 'builtins.str', expr.line, expr.column,
@@ -133,7 +142,7 @@ def expr_to_unanalyzed_type(expr: Expression, _parent: Optional[Expression] = No
         return parse_type_string(expr.value, 'builtins.unicode', expr.line, expr.column,
                                  assume_str_is_unicode=True)
     elif isinstance(expr, UnaryExpr):
-        typ = expr_to_unanalyzed_type(expr.expr)
+        typ = expr_to_unanalyzed_type(expr.expr, options)
         if isinstance(typ, RawExpressionType):
             if isinstance(typ.literal_value, int) and expr.op == '-':
                 typ.literal_value *= -1
diff --git a/mypy/plugins/attrs.py b/mypy/plugins/attrs.py
index c1340e6eaf645..c786ca7a8ce2c 100644
--- a/mypy/plugins/attrs.py
+++ b/mypy/plugins/attrs.py
@@ -552,7 +552,7 @@ def _attribute_from_attrib_maker(ctx: 'mypy.plugin.ClassDefContext',
     type_arg = _get_argument(rvalue, 'type')
     if type_arg and not init_type:
         try:
-            un_type = expr_to_unanalyzed_type(type_arg)
+            un_type = expr_to_unanalyzed_type(type_arg, ctx.api.options)
         except TypeTranslationError:
             ctx.api.fail('Invalid argument to type', type_arg)
         else:
diff --git a/mypy/semanal.py b/mypy/semanal.py
index 96ef7401bf421..8f479ec93304c 100644
--- a/mypy/semanal.py
+++ b/mypy/semanal.py
@@ -1267,7 +1267,7 @@ class Foo(Bar, Generic[T]): ...
             self.analyze_type_expr(base_expr)
 
             try:
-                base = expr_to_unanalyzed_type(base_expr)
+                base = expr_to_unanalyzed_type(base_expr, self.options)
             except TypeTranslationError:
                 # This error will be caught later.
                 continue
@@ -1373,7 +1373,7 @@ def get_all_bases_tvars(self,
         for i, base_expr in enumerate(base_type_exprs):
             if i not in removed:
                 try:
-                    base = expr_to_unanalyzed_type(base_expr)
+                    base = expr_to_unanalyzed_type(base_expr, self.options)
                 except TypeTranslationError:
                     # This error will be caught later.
                     continue
@@ -2101,7 +2101,7 @@ def should_wait_rhs(self, rv: Expression) -> bool:
             return self.should_wait_rhs(rv.callee)
         return False
 
-    def can_be_type_alias(self, rv: Expression) -> bool:
+    def can_be_type_alias(self, rv: Expression, allow_none: bool = False) -> bool:
         """Is this a valid r.h.s. for an alias definition?
 
         Note: this function should be only called for expressions where self.should_wait_rhs()
@@ -2113,6 +2113,13 @@ def can_be_type_alias(self, rv: Expression) -> bool:
             return True
         if self.is_none_alias(rv):
             return True
+        if allow_none and isinstance(rv, NameExpr) and rv.fullname == 'builtins.None':
+            return True
+        if (isinstance(rv, OpExpr)
+                and rv.op == '|'
+                and self.can_be_type_alias(rv.left, allow_none=True)
+                and self.can_be_type_alias(rv.right, allow_none=True)):
+            return True
         return False
 
     def is_type_ref(self, rv: Expression, bare: bool = False) -> bool:
@@ -3195,7 +3202,7 @@ def analyze_value_types(self, items: List[Expression]) -> List[Type]:
         result: List[Type] = []
         for node in items:
             try:
-                analyzed = self.anal_type(expr_to_unanalyzed_type(node),
+                analyzed = self.anal_type(expr_to_unanalyzed_type(node, self.options),
                                           allow_placeholder=True)
                 if analyzed is None:
                     # Type variables are special: we need to place them in the symbol table
@@ -3638,7 +3645,7 @@ def visit_call_expr(self, expr: CallExpr) -> None:
                 return
             # Translate first argument to an unanalyzed type.
             try:
-                target = expr_to_unanalyzed_type(expr.args[0])
+                target = expr_to_unanalyzed_type(expr.args[0], self.options)
             except TypeTranslationError:
                 self.fail('Cast target is not a type', expr)
                 return
@@ -3696,7 +3703,7 @@ def visit_call_expr(self, expr: CallExpr) -> None:
                 return
             # Translate first argument to an unanalyzed type.
             try:
-                target = expr_to_unanalyzed_type(expr.args[0])
+                target = expr_to_unanalyzed_type(expr.args[0], self.options)
             except TypeTranslationError:
                 self.fail('Argument 1 to _promote is not a type', expr)
                 return
@@ -3892,7 +3899,7 @@ def analyze_type_application_args(self, expr: IndexExpr) -> Optional[List[Type]]
             items = [index]
         for item in items:
             try:
-                typearg = expr_to_unanalyzed_type(item)
+                typearg = expr_to_unanalyzed_type(item, self.options)
             except TypeTranslationError:
                 self.fail('Type expected within [...]', expr)
                 return None
@@ -4199,7 +4206,7 @@ def lookup_qualified(self, name: str, ctx: Context,
 
     def lookup_type_node(self, expr: Expression) -> Optional[SymbolTableNode]:
         try:
-            t = expr_to_unanalyzed_type(expr)
+            t = expr_to_unanalyzed_type(expr, self.options)
         except TypeTranslationError:
             return None
         if isinstance(t, UnboundType):
@@ -4919,7 +4926,7 @@ def expr_to_analyzed_type(self,
             assert info.tuple_type, "NamedTuple without tuple type"
             fallback = Instance(info, [])
             return TupleType(info.tuple_type.items, fallback=fallback)
-        typ = expr_to_unanalyzed_type(expr)
+        typ = expr_to_unanalyzed_type(expr, self.options)
         return self.anal_type(typ, report_invalid_types=report_invalid_types,
                               allow_placeholder=allow_placeholder)
 
diff --git a/mypy/semanal_namedtuple.py b/mypy/semanal_namedtuple.py
index 227a038df5f6d..2382ae633d934 100644
--- a/mypy/semanal_namedtuple.py
+++ b/mypy/semanal_namedtuple.py
@@ -356,7 +356,7 @@ def parse_namedtuple_fields_with_types(self, nodes: List[Expression], context: C
                     self.fail("Invalid NamedTuple() field name", item)
                     return None
                 try:
-                    type = expr_to_unanalyzed_type(type_node)
+                    type = expr_to_unanalyzed_type(type_node, self.options)
                 except TypeTranslationError:
                     self.fail('Invalid field type', type_node)
                     return None
diff --git a/mypy/semanal_newtype.py b/mypy/semanal_newtype.py
index 7af348dd281b1..0360cbb86dab5 100644
--- a/mypy/semanal_newtype.py
+++ b/mypy/semanal_newtype.py
@@ -160,7 +160,7 @@ def check_newtype_args(self, name: str, call: CallExpr,
         # Check second argument
         msg = "Argument 2 to NewType(...) must be a valid type"
         try:
-            unanalyzed_type = expr_to_unanalyzed_type(args[1])
+            unanalyzed_type = expr_to_unanalyzed_type(args[1], self.options)
         except TypeTranslationError:
             self.fail(msg, context)
             return None, False
diff --git a/mypy/semanal_typeddict.py b/mypy/semanal_typeddict.py
index d954529c1b14a..3ab4e6d698d5d 100644
--- a/mypy/semanal_typeddict.py
+++ b/mypy/semanal_typeddict.py
@@ -290,7 +290,7 @@ def parse_typeddict_fields_with_types(
                 self.fail_typeddict_arg("Invalid TypedDict() field name", name_context)
                 return [], [], False
             try:
-                type = expr_to_unanalyzed_type(field_type_expr)
+                type = expr_to_unanalyzed_type(field_type_expr, self.options)
             except TypeTranslationError:
                 self.fail_typeddict_arg('Invalid field type', field_type_expr)
                 return [], [], False
diff --git a/mypy/typeanal.py b/mypy/typeanal.py
index 503a9bb99cf5d..45a9960f6dc23 100644
--- a/mypy/typeanal.py
+++ b/mypy/typeanal.py
@@ -80,7 +80,7 @@ def analyze_type_alias(node: Expression,
     Return None otherwise. 'node' must have been semantically analyzed.
     """
     try:
-        type = expr_to_unanalyzed_type(node)
+        type = expr_to_unanalyzed_type(node, options)
     except TypeTranslationError:
         api.fail('Invalid type alias: expression is not a valid type', node)
         return None
diff --git a/test-data/unit/check-classes.test b/test-data/unit/check-classes.test
index b003bf731719e..953a545c5dd0f 100644
--- a/test-data/unit/check-classes.test
+++ b/test-data/unit/check-classes.test
@@ -3154,7 +3154,7 @@ def foo(arg: Type[Any]):
 from typing import Type, Any
 def foo(arg: Type[Any]):
     reveal_type(arg.__str__)  # N: Revealed type is "def () -> builtins.str"
-    reveal_type(arg.mro())  # N: Revealed type is "builtins.list[builtins.type]"
+    reveal_type(arg.mro())  # N: Revealed type is "builtins.list[builtins.type[Any]]"
 [builtins fixtures/type.pyi]
 [out]
 
diff --git a/test-data/unit/check-union-or-syntax.test b/test-data/unit/check-union-or-syntax.test
index 11dff95231626..07edc6bd8d6c5 100644
--- a/test-data/unit/check-union-or-syntax.test
+++ b/test-data/unit/check-union-or-syntax.test
@@ -11,7 +11,6 @@ def f(x: int | str) -> int | str:
 reveal_type(f)  # N: Revealed type is "def (x: Union[builtins.int, builtins.str]) -> Union[builtins.int, builtins.str]"
 [builtins fixtures/tuple.pyi]
 
-
 [case testUnionOrSyntaxWithThreeBuiltinsTypes]
 # flags: --python-version 3.10
 def f(x: int | str | float) -> int | str | float:
@@ -21,7 +20,6 @@ def f(x: int | str | float) -> int | str | float:
     return x
 reveal_type(f)  # N: Revealed type is "def (x: Union[builtins.int, builtins.str, builtins.float]) -> Union[builtins.int, builtins.str, builtins.float]"
 
-
 [case testUnionOrSyntaxWithTwoTypes]
 # flags: --python-version 3.10
 class A: pass
@@ -33,7 +31,6 @@ def f(x: A | B) -> A | B:
     return x
 reveal_type(f)  # N: Revealed type is "def (x: Union[__main__.A, __main__.B]) -> Union[__main__.A, __main__.B]"
 
-
 [case testUnionOrSyntaxWithThreeTypes]
 # flags: --python-version 3.10
 class A: pass
@@ -46,26 +43,22 @@ def f(x: A | B | C) -> A | B | C:
     return x
 reveal_type(f)  # N: Revealed type is "def (x: Union[__main__.A, __main__.B, __main__.C]) -> Union[__main__.A, __main__.B, __main__.C]"
 
-
 [case testUnionOrSyntaxWithLiteral]
 # flags: --python-version 3.10
 from typing_extensions import Literal
 reveal_type(Literal[4] | str)  # N: Revealed type is "Any"
 [builtins fixtures/tuple.pyi]
 
-
 [case testUnionOrSyntaxWithBadOperator]
 # flags: --python-version 3.10
 x: 1 + 2  # E: Invalid type comment or annotation
 
-
 [case testUnionOrSyntaxWithBadOperands]
 # flags: --python-version 3.10
 x: int | 42  # E: Invalid type: try using Literal[42] instead?
 y: 42 | int  # E: Invalid type: try using Literal[42] instead?
 z: str | 42 | int  # E: Invalid type: try using Literal[42] instead?
 
-
 [case testUnionOrSyntaxWithGenerics]
 # flags: --python-version 3.10
 from typing import List
@@ -73,7 +66,6 @@ x: List[int | str]
 reveal_type(x)  # N: Revealed type is "builtins.list[Union[builtins.int, builtins.str]]"
 [builtins fixtures/list.pyi]
 
-
 [case testUnionOrSyntaxWithQuotedFunctionTypes]
 # flags: --python-version 3.4
 from typing import Union
@@ -87,47 +79,79 @@ def g(x: "int | str | None") -> "int | None":
     return 42
 reveal_type(g)  # N: Revealed type is "def (x: Union[builtins.int, builtins.str, None]) -> Union[builtins.int, None]"
 
-
 [case testUnionOrSyntaxWithQuotedVariableTypes]
 # flags: --python-version 3.6
 y: "int | str" = 42
 reveal_type(y)  # N: Revealed type is "Union[builtins.int, builtins.str]"
 
-
 [case testUnionOrSyntaxWithTypeAliasWorking]
 # flags: --python-version 3.10
-from typing import Union
-T = Union[int, str]
+T = int | str
 x: T
 reveal_type(x)  # N: Revealed type is "Union[builtins.int, builtins.str]"
+S = list[int] | str | None
+y: S
+reveal_type(y)  # N: Revealed type is "Union[builtins.list[builtins.int], builtins.str, None]"
+U = str | None
+z: U
+reveal_type(z)  # N: Revealed type is "Union[builtins.str, None]"
+
+def f(): pass
 
+X = int | str | f()
+b: X  # E: Variable "__main__.X" is not valid as a type \
+    # N: See https://mypy.readthedocs.io/en/stable/common_issues.html#variables-vs-type-aliases
+[builtins fixtures/type.pyi]
 
-[case testUnionOrSyntaxWithTypeAliasNotAllowed]
+[case testUnionOrSyntaxWithinRuntimeContextNotAllowed]
 # flags: --python-version 3.9
 from __future__ import annotations
-T = int | str  # E: Unsupported left operand type for | ("Type[int]")
+from typing import List
+T = int | str  # E: Invalid type alias: expression is not a valid type \
+               # E: Unsupported left operand type for | ("Type[int]")
+class C(List[int | str]):  # E: Type expected within [...] \
+                           # E: Invalid base class "List"
+    pass
+C()
 [builtins fixtures/tuple.pyi]
 
+[case testUnionOrSyntaxWithinRuntimeContextNotAllowed2]
+# flags: --python-version 3.9
+from __future__ import annotations
+from typing import cast
+cast(str | int, 'x')  # E: Cast target is not a type
+[builtins fixtures/tuple.pyi]
+[typing fixtures/typing-full.pyi]
 
 [case testUnionOrSyntaxInComment]
 # flags: --python-version 3.6
 x = 1  # type: int | str
 
-
 [case testUnionOrSyntaxFutureImport]
 # flags: --python-version 3.7
 from __future__ import annotations
 x: int | None
 [builtins fixtures/tuple.pyi]
 
-
 [case testUnionOrSyntaxMissingFutureImport]
 # flags: --python-version 3.9
 x: int | None  # E: X | Y syntax for unions requires Python 3.10
 
-
 [case testUnionOrSyntaxInStubFile]
 # flags: --python-version 3.6
 from lib import x
 [file lib.pyi]
 x: int | None
+
+[case testUnionOrSyntaxInMiscRuntimeContexts]
+# flags: --python-version 3.10
+from typing import cast
+
+class C(list[int | None]):
+    pass
+
+def f() -> object: pass
+
+reveal_type(cast(str | None, f()))  # N: Revealed type is "Union[builtins.str, None]"
+reveal_type(list[str | None]())  # N: Revealed type is "builtins.list[Union[builtins.str, None]]"
+[builtins fixtures/type.pyi]
diff --git a/test-data/unit/fixtures/type.pyi b/test-data/unit/fixtures/type.pyi
index 35cf0ad3ce732..755b45ff0bb56 100644
--- a/test-data/unit/fixtures/type.pyi
+++ b/test-data/unit/fixtures/type.pyi
@@ -1,6 +1,6 @@
 # builtins stub used in type-related test cases.
 
-from typing import Generic, TypeVar, List
+from typing import Generic, TypeVar, List, Union
 
 T = TypeVar('T')
 
@@ -10,8 +10,9 @@ class object:
 
 class list(Generic[T]): pass
 
-class type:
+class type(Generic[T]):
     __name__: str
+    def __or__(self, other: Union[type, None]) -> type: pass
     def mro(self) -> List['type']: pass
 
 class tuple(Generic[T]): pass
diff --git a/test-data/unit/fixtures/typing-full.pyi b/test-data/unit/fixtures/typing-full.pyi
index 6aa2f9d291bb7..3de9f934b2554 100644
--- a/test-data/unit/fixtures/typing-full.pyi
+++ b/test-data/unit/fixtures/typing-full.pyi
@@ -10,7 +10,7 @@ from abc import abstractmethod, ABCMeta
 
 class GenericMeta(type): pass
 
-cast = 0
+def cast(t, o): ...
 overload = 0
 Any = 0
 Union = 0