Tritylamine as an Ammonia Surrogate in the Ugi Reaction Provides Access to Unprecedented 5-Sulfamido Oxazoles Using Burgess-type Reagents | Zendy

Irene Preet Bhela | Zendy; M. Teresa Serafini | Zendy; Erika Del Grosso | Zendy; Gian Cesare Tron | Zendy; Tracey Pirali | Zendy

Open Access

Tritylamine as an Ammonia Surrogate in the Ugi Reaction Provides Access to Unprecedented 5-Sulfamido Oxazoles Using Burgess-type Reagents

Author(s) -

Irene Preet Bhela,

M. Teresa Serafini,

Erika Del Grosso,

Gian Cesare Tron,

Tracey Pirali

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c01002

Subject(s) - oxazole , chemistry , reagent , moiety , amide , ugi reaction , combinatorial chemistry , sulfamide , reaction conditions , ammonia , organic chemistry , isocyanide , catalysis

Starting from a wide range of α-acylamino amide substructures synthesized using tritylamine as an ammonia surrogate in the Ugi reaction, Burgess-type reagents enable cyclodehydration and afford unprecedented oxazole scaffolds with four points of diversity, including a sulfamide moiety in the 5-position. The synthetic procedure employs readily available starting materials and proceeds smoothly under mild reaction conditions with good tolerance for a variety of functional groups, coming to fill a gap in the field of oxazole compounds.

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