Hetero Diels-Alder reactions of nitrosoamidines: an efficient method for the synthesis of functionalized guanidines.
Hetero Diels-Alder reactions of transient nitrosoamidines are reported. Transient nitrosoamidines are formed by oxidation of protected N-hydroxylguanidines and are trapped in situ by 1,3-dienes to give [4 + 2] cycloadducts in good yields and regioselectivity. The resultant cycloadducts are versatile intermediates for the formation of functionalized guanidines. [reaction: see text]
Miller
Craig A
CA
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
Batey
Robert A
RA
D000578:Amidines / Q000737:chemistry*; D003500:Cyclization; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009603:Nitroso Compounds / Q000737:chemistry*
D000578:Amidines; D006146:Guanidines; D009603:Nitroso Compounds