Journal
ACS COMBINATORIAL SCIENCE
Volume 16, Issue 5, Pages 221-224Publisher
AMER CHEMICAL SOC
DOI: 10.1021/co400119c
Keywords
anagrelide analogues; cyclic guanidines; Fmoc-amino acids; 2-nitrobenzenesulfonyl chlorides; solid-phase synthesis; cyclative cleavage
Funding
- European Social Fund [CZ.1.07/2.3.00/20.0009, CZ.1.07/2.3.00/30.0060, CZ.1.07/2.4.00/31.0130]
- Palacky University [PrF_2012_023, PrF_2013_027]
- Operational Program Research and Development for Innovations [CZ.1.05/2.1.00/01.0030]
- [CZ.1.07/2.4.00/17.0015]
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Simple solid-phase synthesis of 3,10-dihydro-2H-benzo [e] imidazo [1,2-b] [1,2,4]thiadiazin-2-one 5,5-dioxides is described, with Fmoc-a-amino acids and 2-nitrobenzenesulfonyl chlorides (2-NosCls) being the key building blocks. Fmoc-a-amino acids were immobilized on Wang resin and transformed to the corresponding 2-nitrobenzenesulfonamides in two steps. After reduction of the nitro group, Fmoc-thioureas were synthesized followed by cyclization of the 1,2,4-benzothiadiazine-1,1-dioxide scaffold with diisopropylcarbodiimide (DIC). Cleavage of the Fmoc protecting group followed by spontaneous cyclative cleavage gave the target products in excellent crude purity.
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