re = /(?<=^# .*⤵(?:\n(?!# ).*)*)\n(^## .*)\n(?!#+ )(.*(?:\n(?!#).*)*)/m
str = '# Heading 1 ⤵
## Heading 1.1
Text of Heading 1.1
Text can span over multiple lines
Even more text
## Heading 1.2
Text of Heading 1.2
# Heading 2
## Heading 2.1
Text of Heading 2.1
## Heading 2.2
Text of Heading 2.2
# Heading 3 ⤵
## Heading 3.1
Text of Heading 3.1
## Heading 3.2
Text of Heading 3.2
# Heading 4'
# Print the match result
str.scan(re) do |match|
puts match.to_s
end
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html