HCID 12699163, compound → HCID 20566540, compound

HRID 1732785Notes

Reaction equation

HRID 1732785 reaction equation
C[CH:2]1[CH2:8][CH:7]2[CH:3]1[N:4]([C:13](=[O:15])[CH3:14])[C:5](=[O:12])[N:6]2[C:9](=[O:11])[CH3:10].CC1(C)CC2C1N([C:28](=[O:30])[CH3:29])C(=O)N2C(=O)C.C(C1CC2C1N(C(=O)C)C(=O)N2C(=[O:45])C)(C)(C)C.CC1(C)C(C)(C)C2C1N(C(=O)C)C(=O)N2C(=O)C.C=C1CC2C1N(C(=O)C)C(=O)N2C(=O)C.COC1CC2C1N(C(=O)C)C(=O)N2C(=O)C>>[C:28]([O:30][CH:2]1[CH2:8][CH:7]2[CH:3]1[N:4]([C:13](=[O:15])[CH3:14])[C:5](=[O:12])[N:6]2[C:9](=[O:11])[CH3:10])(=[O:45])[CH3:29]

Participants

7

Reactant 6

HCID 12699163HCID 12699163, compoundHCID 12699172HCID 12699172, compoundHCID 12699173HCID 12699173, compoundHCID 12699174HCID 12699174, compoundHCID 20566538HCID 20566538, compoundHCID 20566542HCID 20566542, compound

Product 1

HCID 20566540HCID 20566540, compoundYield 40%

Procedure

The following cycloadducts are accessible analogously: 6-methyl-2,4-diacetyl-2,4-diaza-bicyclo[3,2,0]heptan-3-one, boiling point0.25 111°-115° (77%); 6,6-dimethyl-2,4-diacetyl-2,4-diaza-bicyclo[3,2,0]heptan-3-one, boiling point0.4 103°-104° (67%); 6-tert.-butyl-2,4-diacetyl-2,4-diaza-bicyclo[3,2,0]heptan-3-one, melting point 85°-86° (54%); 6,6,7,7-tetramethyl-2,4-diacetyl-2,4-diaza-bicyclo[3,2,0]heptan-3-one, melting point 79°-81° (78%); 6-methylene-2,4-diacetyl-2,4-diaza-bicyclo[3,2,0]heptan-3-one, melting point 109°-111° (71%); 6-methoxy-2,4-diacetyl-2,4-diaza-bicyclo[3,2,0]heptan-3-one, boiling point1 120-124 (68%), stereoisomers; 6-acetoxy-2,4-diacetyl-2,4-diaza-bicyclo[3,2,0]heptan-3-one, melting point 151°-153° (single stereoisomer) (82% total yield); 8,10-diacetyl-8,10-diaza-tricyclo[5,3,0,02,6 ]decan-9-one, melting point 148°-150° (single stereoisomer, yield: 40%); and 2',4'-diacetyl-spiro[cyclopropane-1,6'-diaza-(2',4')-bicyclo[3,2,0]heptan-3'-one], melting point 63° (74%).

Workup

  1. customboiling point0.25 111°-115°
  2. customboiling point0.4 103°-104°

Sources & evidence

ORD record
ord-3d8d419a46954643a1ccfd66a2fc434d
Source dataset
uspto-grants-1980_12
Patent number
US04238618

Reaction notes

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