Efficient lactam synthesis
AssigneeUniversity of South Florida
InventorsKyung Woon Jung, Cheol Hwan Yoon
Life of this patent
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Abstract
Lactams, libraries of lactams, and an efficient method of synthesizing a lactam, including a γ-lactam, in which an α-diazoacetamide of the general structure (I) is reacted under conditions promoting intramolecular C—H insertion, for example in the presence of a rhodiurn salt such as Rh2(OAc)4, 1 by which means lactams that are precursors in the synthesis of diverse natural and synthetic products, including pyrrolidinone compounds such as lactacystin, pramanicin, kainic acid, statine, AHPPA, and rolipram, are produced.
Claims8
A method of synthesizing a lactam or a pyrrolidinone precursor of structure (II) said method comprising:
- providing an α-diazoacetamide of structure (I),
- 64
- in which:
- R1, R4, R5, and R6, are independently H, halo, N3, CN, NC, (C1-C22)alkyl, (C6-C10)aryl, (C3-C8)cycloalkyl, (C7-C32)aralkyl, (C7-C32)alkylaryl, OR, SR, N(R)2, CO2R, C(O)R, P(O)(OR)2, COR, CF3, S(O)R, or SO2R, wherein each R is independently H, (C1-C22)alkyl, (C6-C10)aryl, (C3-C8)cycloalkyl, (C2-C22)alkenyl, (C5-C8)cycloalkenyl, (C7-C32)aralkyl, (C7-C32)alkylaryl, (C9-C32)aralkenyl, or (C9-C32)alkenylaryl;
- and
- R2 and R3 together comprise —C(CH3)2—O—CH2—, —(CH2)n—O—C(O)—, or —C(X)—O—CH2— where n=0-10, and X is (C6-C10)aryl or (C7-C32)alkylaryl;
- or R2 and R3 are independently H, halo, N3, CN, NC, (C1-C22)alkyl, (C6-C10)aryl, (C3-C9)cycloalkyl, (C2-C22)alkenyl, (C5-C8)cycloalkenyl, (C7-C32)aralkyl, (C7-C32)alkylaryl, (C9-C32)aralkenyl, (C9-C32)alkenylaryl, OR, SR, N(R)2, NH(R), CO2R, C(O)R, P(O)(OR)2, COR, CF3, S(O)R, or SO2R, wherein each R is independently H, (C1-C22)alkyl, (C6-C10)aryl, (C3-C8)cycloalkyl, (C2-C22)alkenyl, (C5-C8)cycloalkenyl, (C7-C32)aralkyl, (C7-C32)alkylaryl, (C9-C32)aralkenyl, or (C9-C32)alkenylaryl;
- and
- reacting said α-diazoacetamide under conditions promoting intramolecular C—H insertion, whereby said lactam or said pyrrolidinone precursor is synthesized.
Dependencies are inferred from the claim text.