497:
203:
20:
530:
144:
442:
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169:
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533: Lactam Lactim
379:
within the same molecule. Lactamization is most efficient in this way if the product is a γ-lactam. For example, Fmoc-Dab(Mtt)-OH, although its side-chain amine is sterically protected by extremely bulky 4-Methyltrityl (Mtt) group, the amine can still intramolecularly
487:(CSI) can be utilized to obtain both β- as well as γ-lactam. At lower temp (−78 °C), β-lactam is the preferred product. At optimum temperatures, a highly useful γ-lactam known as
701:
pp 4642–4686."2-Azabicyclohept-5-en-3-one: Chemical
Profile of a Versatile Synthetic Building Block and its Impact on the Development of Therapeutics"
496:
384:
with the carboxylic acid to form a γ-lactam. This reaction almost finished within 5 minutes with many coupling reagents (e.g.
752:
441:
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454:
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401:
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324:
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202:
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19:
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642:
634:
466:
352:
301:
131:
757:
626:
344:
615:"Incorporation of Fmoc-Dab(Mtt)-OH during solid-phase peptide synthesis: a word of caution"
39:. Their common names are β-propiolactam, γ-butyrolactam, δ-valerolactam, and ε-caprolactam.
529:
480:
376:
104:
48:
273:
143:
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488:
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116:
593:
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36:
32:
28:
24:
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433:
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320:
563:
389:
381:
372:
77:
55:
51:
18:
385:
516:
compound characterized by an endocyclic carbon-nitrogen
292:
and that of a β-Lactam gives a β-amino acid, and so on.
23:
From left to right, the above are general structures of
613:
Lam, Pak-Lun; Wu, Yue; Wong, Ka-Leung (30 March 2022).
284:
This ring-size nomenclature stems from the fact that
351:, which upon treatment with excess acid forms
8:
347:. Cyclohexanone with hydrazoic acid, forms
300:General synthetic methods are used for the
92:in alphabetical order indicate ring size.
528:
396:Intramolecular nucleophilic substitution
272:
238:
201:
167:
142:
94:
605:
520:. They are formed when lactams undergo
7:
619:Organic & Biomolecular Chemistry
14:
453:Lactams form by copper-catalyzed
428:formed in situ by reaction of an
730:
495:
440:
712:Phosphorus, Sulphur and Silicon
667:Spencer Knapp, Frank S. Gibson
100:(number of atoms in the ring)
1:
371:via the coupling between an
363:Lactams can be formed from
54:, formally derived from an
774:
545:Lactams can polymerize to
359:Cyclization of amino acids
288:of an α-lactam gives an α-
504:Lactam–lactim tautomerism
485:chlorosulfonyl isocyanate
455:1,3-dipolar cycloaddition
65:reactions. The term is a
410:nucleophilic abstraction
710:Pham, P.-T.; Vince, R.
671:, Coll. Vol. 9, p.516 (
406:linear acyl derivatives
534:
355:, a heart stimulant.
325:Beckmann rearrangement
308:Beckmann rearrangement
277:
243:
206:
172:
147:
40:
691:Singh, R.; Vince, R.
532:
402:intramolecular attack
276:
242:
205:
171:
146:
22:
739:at Wikimedia Commons
575:β-Lactam antibiotics
477:Diels-Alder reaction
472:Diels-Alder reaction
312:Lactams form by the
675:); Vol. 70, p.101 (
631:10.1039/D2OB00070A
535:
424:ion reacts with a
400:Lactams form from
335:Lactams form from
278:
244:
207:
173:
148:
41:
753:Functional groups
735:Media related to
669:Organic Syntheses
625:(13): 2601–2604.
577:, which includes
467:Kinugasa reaction
449:Kinugasa reaction
416:Iodolactamization
302:organic synthesis
282:
281:
186:Pyrrolidin-2-one
765:
734:
718:
708:
702:
689:
683:
665:
659:
658:
610:
499:
444:
345:Schmidt reaction
331:Schmidt reaction
220:Piperidin-2-one
119:
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542:
522:tautomerization
506:
481:cyclopentadiene
474:
451:
418:
398:
377:carboxylic acid
361:
349:ε - Caprolactum
333:
310:
298:
269:
235:
198:
164:β-Propiolactam
161:Azetidin-2-one
136:Aziridin-2-one
115:
105:Systematic name
103:
99:
87:
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12:
11:
5:
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725:External links
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681:Online article
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589:2-Piperidinone
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417:
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341:hydrazoic acid
337:cyclic ketones
332:
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314:acid-catalyzed
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229:2-Piperidinone
227:
226:δ-Valerolactam
223:
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209:
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197:
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192:γ-Butyrolactam
189:
187:
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162:
159:
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150:
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139:α-Acetolactam
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113:
108:
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90:Greek prefixes
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83:
15:
13:
10:
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584:2-Pyrrolidone
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539:
531:
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511:
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498:
494:
493:
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491:is obtained.
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318:
317:rearrangement
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295:
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275:
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263:ε-Caprolactam
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259:
257:Azepan-2-one
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195:2-Pyrrolidone
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69:of the words
68:
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59:alkanoic acid
57:
53:
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46:
38:
34:
30:
26:
21:
714:
711:
706:
698:
695:
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687:
676:
672:
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622:
618:
608:
512:is a cyclic
509:
507:
489:Vince Lactam
475:
452:
426:halonium ion
419:
399:
362:
334:
311:
304:of lactams.
299:
283:
232:2-piperidone
88:
85:Nomenclature
76:
70:
44:
42:
16:Cyclic amide
594:Caprolactam
579:penicillins
562:, a cyclic
518:double bond
514:imidic acid
369:amino acids
365:cyclisation
266:Caprolactam
117:Common name
67:portmanteau
63:cyclization
747:Categories
717:, 779-791.
693:Chem. Rev.
600:References
547:polyamides
412:reaction.
353:Cardiazole
290:amino acid
286:hydrolysis
123:Structure
111:IUPAC name
655:247175352
639:1477-0539
540:Reactions
408:from the
296:Synthesis
98:Ring size
699:112 (8),
647:35258068
570:β-Lactam
554:See also
479:between
463:nitrones
253:ε-Lactam
216:δ-Lactam
182:γ-Lactam
157:β-Lactam
132:α-Lactam
61:through
37:ε-lactam
33:δ-lactam
29:γ-lactam
25:β-lactam
758:Lactams
737:Lactams
560:Lactone
465:in the
459:alkynes
422:iminium
343:in the
323:in the
72:lactone
653:
645:
637:
510:lactim
434:iodine
430:alkene
382:couple
375:and a
321:oximes
49:cyclic
45:lactam
35:, and
696:2012,
651:S2CID
564:ester
432:with
390:PyAOP
373:amine
78:amide
56:amino
52:amide
47:is a
715:2007
677:1992
673:1998
643:PMID
635:ISSN
483:and
461:and
388:and
386:HATU
339:and
120:(s)
31:, a
27:, a
627:doi
457:of
420:An
404:of
392:).
367:of
319:of
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508:A
436:.
327:.
249:7
212:6
178:5
153:4
128:3
81:.
75:+
43:A
657:.
629::
566:.
549:.
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