Frenchman Adrian Mannarino came from behind to beat wildcard Roman Safiullin 1-6 7-6 (8-6) 6-4 to book a showdown against top seed Andrey Rublev at the Kremlin Cup in Moscow.
American Tommy Paul beat Sweden’s Mikael Ymer 7-6 (9-7) 7-5, which set up a match against two-time Moscow champion Marin Cilic in round two.
Veteran Frenchman Gilles Simon battled past eighth-seeded Laslo Djere, defeating the Serbian 6-7 (3-7) 7-5 6-3 and Belarus qualifier Egor Gerasimov saw off Miomir Kecmanovic 6-3 1-6 6-4, and goes on to play second seeded Russian Aslan Karatse2.
Spaniard Pedro Martinez led Guido Pella 6-2 when the Argentine retired while lucky loser Ricardas Berankis progressed with a 6-1 6-3 defeat of Russian wildcard Evgeny Donskoy.
Aussie qualifier John Millman will face Ukrainian Iylia Marchenko, who beat No.5 seed Alexander Bublik in straight sets 6-4 6-3.